Mohammad Movassaghi,* Meiliana Tjandra, and Jun Qi Reporter: ZhiYong Han 2009-07-06 Total Synthesis...
-
date post
18-Dec-2015 -
Category
Documents
-
view
213 -
download
1
Transcript of Mohammad Movassaghi,* Meiliana Tjandra, and Jun Qi Reporter: ZhiYong Han 2009-07-06 Total Synthesis...
Mohammad Movassaghi,* Meiliana Tjandra, and Jun Qi
Reporter: ZhiYong HanReporter: ZhiYong Han2009-07-062009-07-06
Total Synthesis of (-)-Himandrine
J. AM. CHEM. SOC ASAP
2
Hzy-090706Author
•Mohammad Movassaghi
•Associate Professor of Chemistry
•Massachusetts Institute of Technology
B.S. University of California at Berkeley 1995 Ph.D. Harvard University 2001
3
Hzy-090706Origin
Galbulimima belgraveana
Cannabis(大麻 )
Similarity
Hallucinogen(迷幻剂 )
Popuans(巴布亚人 )
Sleeping Popuan
Boil
7
Hzy-090706
Tetrakis(triphenylphosphine)palladium (1.54 g, 1.30 mmol, 8.00 mol%) and thalliumcarbonate (15.7 g, 33.0 mmol, 2.00 equiv) were added sequentially
OTBS
B(OH)2
OMe
OTBS
BrOMe
BrBr
+
MacMillan -hydroxylation
Pd(PPh3)4,Tl2CO3
97%
9
Hzy-090706
O H
H
H
OMeN
H
H
O
>50%
N
Me
nBuLi;CuBr·SMe2
OH
H
H
OMeN
H
H
O
NMe
H
OH
H
H
OMeN
H
H
O
NMe
H
H
H
H
H
OMeN
H
H
O
N
OHH
Me
H
H
HH
(-)-15
(-)-19
11
Hzy-090706
H
H
H
H
OMe
H
HN
OHH
MeH
H
OZ
H
H
H
OMe
H
HN
OHH
MeH
H
OHZ
H
H
H
H
OMe
H
N
H
MeH
H
OZ
H
Cl
N
H
O H
H
H
H
OMe
H
NMe
H
H
OZ
OH
NMe2
71%
POCl3DMF
Vilsmeier’sreagent
(-)-21
(+)-23