Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic...

40
Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()- galanthamine. Tetrahedron Letters (2009), 50(34), 4882- 4884.

TAGS:

Transcript of Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic...

Page 1: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34), 4882-4884.

Page 2: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 3: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 4: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 5: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

pKa phenol = 9.9

pKa2 of carbonic acid = 10.33

Page 6: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 7: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 8: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

The Claisen Rearrangment is a [3,3] sigmatropic rearrangement

Aromatic Claisen Rearrangement

Cope Rearrangement is related

Page 9: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

Sigmatropic: One sigma bond is changed to another.

Page 10: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 11: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 12: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 13: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 14: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

pKa conjugate acid of imidazole = 7.2

Page 15: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 16: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

DIPEA = Diisopropylethylamine (Hunig’s Base). This base is more sterically hindered, and thus less nucleophilic, than triethylamine.pKa of the conjugate acid of Hunig’s base = 11.0

MOM = Methoxymethyl MOMCl = H3C-O-CH2-Cl

Page 17: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 18: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

2,6-Lutidine =

pKa conjugate acid of 2,6-lutidine = 6.7

Page 19: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 20: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

pKa hydroxylamine hydrochloride = 6pKa conjugate acid of pyridine = 5.2pKa conjugate acid of triethylamine = 10.6

Page 21: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 22: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

DMPU = Dimethylpropyleneurea = solvent to replace HMPA, a carcinogen

LDA = lithium diisopropylamide pKa of diisopropylamine (conjugate acid of LDA) = 36

pKa acetonitrile = 25pKa phenylacetonitrile = 22

Page 23: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 24: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 25: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 26: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 27: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 28: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

pKa p-toluenesulfonic acid = - 0.4

Page 29: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 30: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 31: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 32: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 33: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 34: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 35: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 36: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 37: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 38: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

DPPA = diphenylphosphoryl azide =

DBU = Diazabicycloundecene =

Conjugate acid of DBU pKa = 13.2

Page 39: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),
Page 40: Chandrasekhar, S.; Basu, Debjit; Sailu, M.; Kotamraju, S. Novel synthetic route to the tricyclic core of ()-galanthamine. Tetrahedron Letters (2009), 50(34),

Page 1 of 77 MAHARASHTRA STATE COUNCIL OF …... · 3 27170804801zpps kupta kupta sailu parabhani 431503 8390920347 8390920347 marathi m1540602035 prathmesh ganeshrao solanke m gen

Page 1 of 77 MAHARASHTRA STATE COUNCIL OF …... · 3 27170804801zpps kupta kupta sailu parabhani 431503 8390920347 8390920347 marathi m1540602035 prathmesh ganeshrao solanke m gen

Catalytic Asymmetric Total Syntheses of (-)-Galanthamine and (-) …ccc.chem.pitt.edu/wipf/Current Literature/Lalith_2.pdf · 2015-06-21 · HOH H O O N Boc OH O O N Boc O O O O O

Catalytic Asymmetric Total Syntheses of (-)-Galanthamine and (-) …ccc.chem.pitt.edu/wipf/Current Literature/Lalith_2.pdf · 2015-06-21 · HOH H O O N Boc OH O O N Boc O O O O O

An Extraction Assay Analysis for Galanthamine in …...Volume 3 • Issue 5 • 1000144 J Anal Bioanal Techniques ISSN:2155-9872 JABT, an open access journal Citation: Steiner WE,

An Extraction Assay Analysis for Galanthamine in …...Volume 3 • Issue 5 • 1000144 J Anal Bioanal Techniques ISSN:2155-9872 JABT, an open access journal Citation: Steiner WE,

List of Posters ICNPU-20177 of Posters ICNPU-2017(1).pdf · Bastida, Carles Codina PP 20: ISOLATION OF GENES INVOLVED IN GALANTHAMINE BIOSYNTHESIS Ivelin Panchev, Ilian Badjakov,

List of Posters ICNPU-20177 of Posters ICNPU-2017(1).pdf · Bastida, Carles Codina PP 20: ISOLATION OF GENES INVOLVED IN GALANTHAMINE BIOSYNTHESIS Ivelin Panchev, Ilian Badjakov,

Pradeep Kotamraju, Deputy Director, NRCCTE Amanda Richards, Senior Research Associate, MPR Inc. Building on the past to improve the future.

Pradeep Kotamraju, Deputy Director, NRCCTE Amanda Richards, Senior Research Associate, MPR Inc. Building on the past to improve the future.

karimnagar.nic.inkarimnagar.nic.in/docs/gangadhara.xls · XLS file · Web viewPulicherla Sailu,, Naresh Amireshetti Narsaiah Jarathi Rajanna Samathula Venkatesham Penchala Mallesham

karimnagar.nic.inkarimnagar.nic.in/docs/gangadhara.xls · XLS file · Web viewPulicherla Sailu,, Naresh Amireshetti Narsaiah Jarathi Rajanna Samathula Venkatesham Penchala Mallesham

A TYPOLOGY FOR UNDERSTANDING THE CAREER … Typology for Understanding the Career and Technical Education Credit-Taking Experience of High School Students Oscar A. Aliaga Pradeep Kotamraju

A TYPOLOGY FOR UNDERSTANDING THE CAREER … Typology for Understanding the Career and Technical Education Credit-Taking Experience of High School Students Oscar A. Aliaga Pradeep Kotamraju

An Organizational Story: Salesforce Lightning Design (Nalini Kotamraju at Enterprise UX 2016)

An Organizational Story: Salesforce Lightning Design (Nalini Kotamraju at Enterprise UX 2016)

Oscar A. Aliaga Pradeep Kotamraju May 16 th , 2012

Oscar A. Aliaga Pradeep Kotamraju May 16 th , 2012

Reproductions supplied by EDRS are the best that can be ... · DOCUMENT RESUME ED 469 189 CE 083 555 AUTHOR Kotamraju, Pradeep; Steuernagel, Bruce; Jacquart, Mary TITLE New Program

Reproductions supplied by EDRS are the best that can be ... · DOCUMENT RESUME ED 469 189 CE 083 555 AUTHOR Kotamraju, Pradeep; Steuernagel, Bruce; Jacquart, Mary TITLE New Program

Inhibitors, Agonists, Screening Librariesupdate.medchemexpress.com/pdf/MCE_Brochure.pdf · 2017. 4. 11. · 3 Target Name Cat. No. A 0-9 Target Name Cat. No. Clozapine Galanthamine

Inhibitors, Agonists, Screening Librariesupdate.medchemexpress.com/pdf/MCE_Brochure.pdf · 2017. 4. 11. · 3 Target Name Cat. No. A 0-9 Target Name Cat. No. Clozapine Galanthamine

Sailu Lifi

Sailu Lifi

Teradyne’s Aurora Project Solving The Innovator’s Dilemma Sailu Challapalli, Michael Chu, Annie Kuo, Emily Liu, Arundhati Singh, Erick Tseng.

Teradyne’s Aurora Project Solving The Innovator’s Dilemma Sailu Challapalli, Michael Chu, Annie Kuo, Emily Liu, Arundhati Singh, Erick Tseng.

Date: 18-7-2018 · 111 110 vadlakonda rajitha 112 111 medi vijay kumar medi sailu 113 112 chava rathna kumari ch venkat rao 114 113 ch satish ch venkat ramulu ... 137 139 ganesh k.

Date: 18-7-2018 · 111 110 vadlakonda rajitha 112 111 medi vijay kumar medi sailu 113 112 chava rathna kumari ch venkat rao 114 113 ch satish ch venkat ramulu ... 137 139 ganesh k.

Emerging Issues of Data Collection in TAACCCT Grant Implementation Presenters: Pradeep Kotamraju Bureau Chief, Career & Technical Education Division of.

Emerging Issues of Data Collection in TAACCCT Grant Implementation Presenters: Pradeep Kotamraju Bureau Chief, Career & Technical Education Division of.

PortNL: An Integrated Service Case Nalini P. Kotamraju, Ph.D. 9 februari 2010.

PortNL: An Integrated Service Case Nalini P. Kotamraju, Ph.D. 9 februari 2010.

Copyright by Benjamin Perry Fauber 2006 · The first total synthesis of galanthamine was reported by Barton and Kirby in 1960. 12 They completed a biomimetic route, in which 4'- O

Copyright by Benjamin Perry Fauber 2006 · The first total synthesis of galanthamine was reported by Barton and Kirby in 1960. 12 They completed a biomimetic route, in which 4'- O

Global Media Coverage - ICRISAT · Using treated wastewater means Serigudam Sailu can now grow coriander as an income source ... with benefits for their income and the land Friday

Global Media Coverage - ICRISAT · Using treated wastewater means Serigudam Sailu can now grow coriander as an income source ... with benefits for their income and the land Friday

Archived: The Relationship Between … · Web viewThe Relationship Between Postsecondary Degree Program Outcomes and Occupational Needs in Minnesota Pradeep Kotamraju, Ph.D. Institutional

Archived: The Relationship Between … · Web viewThe Relationship Between Postsecondary Degree Program Outcomes and Occupational Needs in Minnesota Pradeep Kotamraju, Ph.D. Institutional

vk;lh,evkj&jkVªh; iztuu LokLF; vuqla/kku laLFkku · Rajshree Hemraj Chandekar 1178 P2_446 Sailu Sarvagalla 1179 P2_449 Tiruveedhula Jahnavi 1180 P2_452 P4_115 Urmila Chaudhary 1181

vk;lh,evkj&jkVªh; iztuu LokLF; vuqla/kku laLFkku · Rajshree Hemraj Chandekar 1178 P2_446 Sailu Sarvagalla 1179 P2_449 Tiruveedhula Jahnavi 1180 P2_452 P4_115 Urmila Chaudhary 1181