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Synlett 1995; 1995(8): 850-852
DOI: 10.1055/s-1995-5095
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Stereoselective Synthesis of the Brassinolide Side Chain by the Use of a 5-Exo-α-Silyl Radical Cyclization - Protiodesilylation Sequence

Masato Koreeda* , Junjun Wu
  • *Department of Chemistry, The University of Michigan, Ann Arbor, Michigan 48109-1055, USA
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Publikationsdatum:
31. Dezember 2000 (online)

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The stereoselective synthesis of the steroid having the brassinolide side chain 2 has been achieved from readily available aldehyde 7 in 8 steps and 31% overall yield, featuring a 5-exo-mode of α-silyl radical cyclization - protiodesilylation sequence as a means for the key stereoselective installment of the 24-methyl group.

brassinolide side chain - α-silyl radical cyclization - 5-exo-radical cyclization - 1-sila-2-oxacyclopentane - protiodesilylation