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Synlett 1997; 1997(6): 689-690
DOI: 10.1055/s-1997-3255
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Synthesis of a 14β-Hydroxysteroid Using the Transannular Diels-Alder Strategy

L. Ouellet, P. Langlois, Pierre Deslongchamps*
  • *Laboratoire de synthèse organique, Département de chimie, Faculté des sciences, Université de Sherbrooke, Sherbrooke (QC) Canada J1K 2R1, Fax: (819) 821-7910; e-mail: dlnchamp@structure.chimie.usherb.ca
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Publication Date:
31 December 2000 (online)

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Macrocyclic TCC triene 1, generated by an intramolecular alkylation of a β-ketoester on a π-allylpalladium complex followed by dehydrogenation, underwent a highly stereoselective transannular Diels-Alder reaction affording the tetracyclic compound 2 in an excellent yield.

cardenolides - cardiac glycosides - 14β-hydroxysteroid - transannular Diels-Alder reaction - macrocyclisation