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Synlett 1996; 1996(11): 1140-1142
DOI: 10.1055/s-1996-5686
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Expedient Synthesis of a 5α-Steroid Using the Transannular Diels-Alder Strategy

Michel Couturier, 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 11, generated by a novel intramolecular displacement of the α-chloroketone 10, readily underwent a highly stereoselective transannular Diels-Alder reaction to yield the TSCAT tetracyclic adduct 12, from which the TATAT steroid 13 was obtained through epimerization at C-9.

5α-Steroid - transannular Diels-Alder reaction - α-chloroketone - macrocyclization

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