Strychnos 1990 - 2004 - Crops for the Future

Author
Title
Year
Source title
Reference
Diez, A., J. Castells, P. Forns, M. Rubiralta, D. S. Grierson, H. P. Husson, X. Sola
Synthetic applications of 2-(1,3-dithian-2-yl)indoles .4. New synthesis of the tetra
1994
Tetrahedron
50(22): 6585-6602
Abstract
A new and versatile synthesis of tetracyclic compounds 10, 22 and 24 presenting the ABED ring
system of Strychnos alkaloids is described by closure of the C-1-C-11b bond in the key step. The
intermediate tetrahydropyridinium salts 2 have been obtained from 2-(1,3-dithian-2-yl)indole (3) and
either 2-cyano-3-ethyl-1-methyl-1,2,3,6-tetrahydropyridine (4a) or N-substituted Delta(3)-piperidein-
2 - o n e s ( 5 ) .
Author
Title
Year
Source title
Reference
Gracia, J., N. Casamitjana, J. Bonjoch and J. Bosch
Total synthesis of uleine-type and Strycknos alkaloids through a common interme
1994
Journal of Organic Chemistry
59(14): 3939-3951
Abstract
A stereoselective total synthesis of the alkaloids of the uleine group, dasycarpidone, dasycarpidol,
and nordasycarpidone, has been accomplished from the tetracyclic intermediate 1, which has been
prepared by two alternative routes, either by Fischer indolization of 2-azabicyclo[3.3.1]nonanone 9
or, more efficiently, by stereocontrolled cyclization of 2-[(2-cyano-3-ethyl-4-piperidyl)methyl]i 24a
and 24b. From the same tetracyclic intermediate 1, the Strychnos alkaloid tubotaiwine was also
synthesized, the key step being the construction of the quaternary spiranic center by cyclization of a
t h i o n i u m i o n u p o n t h e i n d o l e b e t a - p o s i t i o n .
Author
Title
Year
Source title
Reference
Abstract
Kraus, G. A. and D. Bougie
The preparation of a hexacyclic intermediate for the synthesis of Strychnos alkaloi
1994
Tetrahedron
50(9): 2681
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