The total synthesis of (+)-ryanodol. Part II. Model studies for rings B and C of (+)-anhydroryanodol. Preparation of a key pentacyclic intermediate

This paper reports several model studies that were necessary for the rational conception of a simple four-step synthesis ( 6  + (S)- 74  →  81 a-b →  83     87  →  89 ) (Scheme 11) of the carbonate derivative 89 of the optically active pentacyclic dihydroxy ketoaldehyde 87 , an important key interme...

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Published inCanadian journal of chemistry Vol. 68; no. 1; pp. 127 - 152
Main 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
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.01.1990
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Summary:This paper reports several model studies that were necessary for the rational conception of a simple four-step synthesis ( 6  + (S)- 74  →  81 a-b →  83     87  →  89 ) (Scheme 11) of the carbonate derivative 89 of the optically active pentacyclic dihydroxy ketoaldehyde 87 , an important key intermediate for the synthesis of (+)-ryanodol ( 5 ). The optically active vinyl ketone (S)- 74 that was used as starting material was prepared in four steps from d-carvone ((S)- 94 ) (Scheme 13). The preparation of the other starting material, the o-spirolactone dienone 6 , was reported in Part I. Keywords: strategy, synthesis, ryanodol, key intermediate, diterpene.
ISSN:0008-4042
1480-3291
DOI:10.1139/v90-022