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Synthesis of (23R)- and (23S)-23H-Isocalysterols, Marine Sterols with a Cyclopropene Moiety in the Side Chain

✍ Scribed by Alicja Kurek-Tyrlik; Kazimierz Minksztym; Jerzy Wicha

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 367 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(200003)2000:6<1027::aid-ejoc1027>3.0.co;2-e

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✦ Synopsis

A synthesis of (23R)-and (23S)-23H-calysterols 2a and 2b from pregnanoic ester 10 is reported. Alkylation of 10 with dibromide 19b, followed by reduction of the carboethyloxy group to a methyl group, afforded (Z)-vinylic bromide 22. Dibromocyclopropanation of 22 yielded the diastereomeric tri-

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