The total synthesis of (+)-ryanodol. Part I. General strategy and search for a convenient diene for the construction of a key tricyclic intermediate

Author:

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

Abstract

This paper reports a retrosynthetic analysis that led to the conception of a synthetic strategy for the construction of ryanodol (2). The preparation of a key diene, i.e., spirolactone dienone 47 (19 → 31 → 33 → 48 → 49 → 52 → 47), and its Diels–Alder reaction with methyl vinyl ketone are reported. Keywords: strategy, synthesis, ryanodol, diterpene.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

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