ChemInform Abstract: A HIGHLY EFFICIENT TOTAL SYNTHESIS OF (.+-.)-LYCOPODINE

1979 ◽  
Vol 10 (12) ◽  
Author(s):  
C. H. HEATHCOCK ◽  
E. KLEINMAN ◽  
E. S. BINKLEY
Keyword(s):  
Total Synthesis ◽  
Highly Efficient

scholarly journals Stereocontrolled total synthesis of (+)-vinblastine

2003 ◽  
Vol 75 (1) ◽  
pp. 29-38 ◽  
Author(s):  
Satoshi Yokoshima ◽  
T. Ueda ◽  
S. Kobayashi ◽  
A. Sato ◽  
Takeshi Kuboyama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Radical Cyclization ◽  
Critical Coupling ◽  
Efficient Manner ◽  
Complete Control ◽  
Highly Efficient ◽  
Indole Synthesis

Stereocontrolled total synthesis of (+)-vinblastine (1) has been achieved using a novel radical-mediated indole synthesis developed in our laboratories. The isothiocyanate 18, prepared readily from quinoline 17, underwent a facile addition of the malonate anion to give 19. The o-alkenylthioanilide 19 was then converted to indole 20 by radical cyclization and protection. (−)-Vindoline (2) was prepared from this key intermediate 20 in a highly efficient manner. The indole core of the 11-membered intermediate 3 was constructed similarly from quinoline. The critical coupling reaction between 2 and the chloroindolenine derived from 3 proceeded with complete control of stereochemistry to give the desired product 66 in 97 % yield, which could be successfully converted to (+)-vinblastine (1).

A highly efficient total synthesis of (.+-.)-lycopodine

1978 ◽  
Vol 100 (25) ◽  
pp. 8036-8037 ◽  
Author(s):  
Clayton H. Heathcock ◽  
Edward Kleinman ◽  
Edward S. Binkley
Keyword(s):  
Total Synthesis ◽  
Highly Efficient

Highly Efficient Stereocontrolled Total Synthesis of (+)-Upial

2008 ◽  
Vol 120 (1) ◽  
pp. 137-139
Author(s):  
Kazunori Takahashi ◽  
Masayuki Watanabe ◽  
Toshio Honda
Keyword(s):  
Total Synthesis ◽  
Highly Efficient
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