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An Intramolecular Furan−Diene Diels−Alder Approach to 11‐Oxo 10α‐Steroids
Author(s) -
Claeys Sandra,
Van Haver Dirk,
De Clercq Pierre J.,
Milanesio Marco,
Viterbo Davide
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200203)2002:6<1051::aid-ejoc1051>3.0.co;2-#
Subject(s) - chemistry , furan , intramolecular force , diels–alder reaction , diene , organic chemistry , stereochemistry , catalysis , natural rubber
The intramolecular cycloaddition of 14 , with dimethylaluminium chloride as a catalyst and under kinetic control, yielded the exo adduct 19a . Opening of the oxygen bridge in the reduced adduct 20 gave intermediate 21 . Oxidation of the latter made it possible to introduce the methyl group at C‐10, which exclusively afforded 23 , with the unnatural configuration. Further conversion resulted in the formation of D‐homo‐10‐ epi ‐adrenosterone ( 25 ). (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)