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

1990; NRC Research Press; Volume: 68; Issue: 1 Linguagem: Inglês

10.1139/v90-023

1480-3291

Pierre Deslongchamps, André Bélanger, Daniel Berney, H.‐J. BORSCHBERG, Robert Brousseau, Alain Doutheau, Robert Durand, Hajime Katayama, Richard Lapalme, Dominique M. Leturc, Chun‐Chen Liao, Frederick N. MacLachlan, Jean‐Pierre Maffrand, Fabrizio Marazza, Robert Martino, Claude Moreau, Luc Ruest, Louiselle Saint-Laurent, Roger Saintonge, Pierre Soucy,

Chemical synthesis and alkaloids

This paper reports several studies that were carried out to learn how to transform the dextrorotatory pentacyclic key intermediate 5 into (+)-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 5 is reported in Parts I and II of this series. Keywords: anhydroryanodol, ryanodol, diterpene, organic synthesis, strategy.