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Synthesis 2000; 2000(12): 1761-1765
DOI: 10.1055/s-2000-8210
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Diels-Alder Cycloadditions of 3-Methoxy-8α-estra-1,3,5(10),14,16-pentaen-17-yl Acetate: Unexpected Trends in Regioselectivity

James R. Bull* , Pieter D. de Koning
  • *Department of Chemistry, University of Cape Town, Private Bag, Rondebosch 7701, South Africa; E-mail: bull@psipsy.uct.ac.za
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Publication Date:
31 December 2000 (online)

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In contrast to Diels-Alder reactions of 3-methoxyestra-1,3,5(10),14,16-pentaen-17-yl acetate, in which 14,17-bridged cycloadducts are formed with high head-to-head β-face selectivity, product distributions for similar reactions of 3-methoxy-8α-estra-1,3,5(10),14,16-pentaen-17-yl acetate display sensitivity to the nature and reactivity of the dienophile, with a trend favouring regioreversal during β-face cycloaddition. Results are interpreted in terms of competing stereoelectronic and steric influences.

Diels-Alder reactions - steroids - regioselectivity - estradiol analogues - chiral cyclopentadienes

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