Interconversion of cembranolide. delta.-and. gamma.-lactones: synthesis of the C-1 epimer of isolobophytolide

JA Marshall, LJ Karas, MJ Coghlan

Index: Marshall, James A.; Karas, Lawrence J.; Coghlan, Michael J. Journal of Organic Chemistry, 1982 , vol. 47, # 4 p. 699 - 701

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Citation Number: 15

Abstract

The &lactone cembranolide diterpene crassin alcohol (2) has been converted to an isomeric y-lactone isocrassin alcohol (6) by a sequence involving kinetically controlled addition of benzenethiol to the conjugated lactone double bond followed by base-promoted translactonization and thermal elimination of the derived sulfoxide. Internal displacement of the monomethanesulfonate derivative 7 of lactone diol 6 afforded epoxy lactone 11, the C- ...