Synthesis of the tricyclic portions of batzelladines A, B and D. Revision of the stereochemistry of batzelladines A and D

The tricyclic portion 4 of batzelladine B ( 2) is obtained from 10a, which differs in one side chain from the ptilomycalin A model 10c that we prepared several years ago, by reduction with NaBH 3CN in buffered MeOH. Hydrogenation of 11b over Rh Al 2O 3 at 50 PSI H 2 affords the proposed tricyclic po...

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Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 39; pp. 6977 - 6980
Main Authors Snider, Barry B, Chen, Jinsheng, Patil, Ashok D, Freyer, Alan J
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.09.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
BIOMIMETIC SYNTHESIS
CRAMBINE-C1
SPONGE CRAMBE-CRAMBE
PTILOMYCALIN-A
GUANIDINE ALKALOIDS
MOIETIES
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Summary:The tricyclic portion 4 of batzelladine B ( 2) is obtained from 10a, which differs in one side chain from the ptilomycalin A model 10c that we prepared several years ago, by reduction with NaBH 3CN in buffered MeOH. Hydrogenation of 11b over Rh Al 2O 3 at 50 PSI H 2 affords the proposed tricyclic portion 12b of batzelladine A ( 1). Epimerization of 12b and hydrolysis affords acid 3, which is similar to, but different from, the acid obtained from hydrolysis of 1. A five step sequence converts 7b to the anti tricyclic acid 15, which is identical to the hydrolysis product of 1. The stereochemistry of the hydrolysis product 15 was confirmed by NOE experiments. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01575-4