STEREOSELECTIVE PREPARATION OF THE ABCD TETRACYCLE OF THE 20-METHYL ANALOG OF ASPIDOSPERMIDINE AND RELATED ALKALOIDS

Authors
URRUTIA A RODRIGUEZ JG
Citation
A. Urrutia et Jg. Rodriguez, STEREOSELECTIVE PREPARATION OF THE ABCD TETRACYCLE OF THE 20-METHYL ANALOG OF ASPIDOSPERMIDINE AND RELATED ALKALOIDS, Tetrahedron letters, 39(23), 1998, pp. 4143-4146
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
23
Year of publication
1998
Pages
4143 - 4146
Database
ISI
SICI code
0040-4039(1998)39:23<4143:SPOTAT>2.0.ZU;2-7
Abstract
The natural cis[ABCD] tetracycle of the 20-methyl analogue of aspidosp ermidine has been synthesised, starting from the 4,4-ethylenedioxy-1-c yclohexanone. This, was transformed into (3'-nitropropyl)-1,2,3,4-tetr ahydrocarbazol-4-one. Two key synthetic steps permits the construction of the D ring: i) the one pot nickel boride catalyst to the imine tet racycle in excellent yield; and ii) the stereoselective reduction of t his imine to the natural cis D ring junction in good yield. (C) 1998 E lsevier Science Ltd. All rights reserved.