The total synthesis of (+)-ryanodol. Part II. Model studies for rings B and C of (+)-anhydroryanodol. Preparation of a key pentacyclic intermediate
1990; NRC Research Press; Volume: 68; Issue: 1 Linguagem: Inglês
10.1139/v90-022
ISSN1480-3291
AutoresPierre 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,
Tópico(s)Axial and Atropisomeric Chirality Synthesis
ResumoThis paper reports several model studies that were necessary for the rational conception of a simple four-step synthesis (6 + (S)-74 → 81a–b → 83 [Formula: see text] 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.
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