SIMPLE TOTAL SYNTHESES OF (-)-ERGOT ALKALOIDS AND THEIR (-ENANTIOMERSBY A COMMON SYNTHESIS METHOD UTILIZING OPTICAL RESOLUTION())

Authors
SOMEI M NAKAGAWA K
Citation
M. Somei et K. Nakagawa, SIMPLE TOTAL SYNTHESES OF (-)-ERGOT ALKALOIDS AND THEIR (-ENANTIOMERSBY A COMMON SYNTHESIS METHOD UTILIZING OPTICAL RESOLUTION()), Heterocycles, 45(7), 1997, pp. 1263-1266
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
7
Year of publication
1997
Pages
1263 - 1266
Database
ISI
SICI code
0385-5414(1997)45:7<1263:STSO(A>2.0.ZU;2-F
Abstract
The first and simple total syntheses of (-)-isochanoclavine-I ((-)-1b) , (-)-agroclavine ((-)-3), (-)-agroclavine-I ((-)-4), and (-)-norchano clavine-I ((-)-5C) and their (+)-enantiomers are achieved from indole- 3-carboxaldehyde (8) by a common synthesis method utilizing optical re solution. Absolute configuration of (-)-agroclavine-I is determined to be 5R and 10S for the first time. Preparations of both enantiomers of chanoclavine-I (1c) are also included.