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The total synthesis of (+)-ryanodol. Part III. Preparation of (+)-anhydroryanodol from a key pentacyclic intermediate

Authors :
Deslongchamps, Pierre
Bélanger, André
Berney, Daniel J. F.
Borschberg, Hans-Juerg
Brousseau, Robert
Doutheau, Alain
Durand, Robert
Katayama, Hajime
Lapalme, Richard
Leturc, Dominique M.
Liao, Chun-Chen
MacLachlan, Frederick N.
Maffrand, Jean-Pierre
Marazza, Fabrizio
Martino, Robert
Moreau, Claude
Ruest, Luc
Saint-Laurent, Louiselle
Saintonge, Roger
Soucy, Pierre
Source :
Canadian Journal of Chemistry; January 1990, Vol. 68 Issue: 1 p153-185, 33p
Publication Year :
1990

Abstract

This paper reports several studies that were carried out to learn how to transform the dextrorotatory pentacyclic key intermediate 5into (+)-anhydroryanodol (6). This transformation requires 24 steps, and takes place via the following intermediates: 5 → 11 → 19 → 34 → 36 → 39 → 144 → 150 → 6. The preparation of the key pentacyclic intermediate 5is reported in Parts I and II of this series. Keywords: anhydroryanodol, ryanodol, diterpene, organic synthesis, strategy.

Details

Language :
English
ISSN :
00084042 and 14803291
Volume :
68
Issue :
1
Database :
Supplemental Index
Journal :
Canadian Journal of Chemistry
Publication Type :
Periodical
Accession number :
ejs19686989
Full Text :
https://doi.org/10.1139/v90-023