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Science in China. Series B, Chemistry, life sciences & earth sciences

Studies on steroidal plant-growth regulators (XVII)--a new synthesis of homobrassinolide and (22S, 23S)-22, 23-epi-homobrassinolide.


PMID 1888437

Abstract

Homobrassinolide (2) and (22S, 23S)-22,23-epi-homobrassinolide (4) were synthesized from stigmasterol in seven steps respectively in 4.7% and 24.1% overall yields. The ratio of 2 to 4 is 1:5. The key step is the highly regioselective formation of the B-homo-7-oxa-lactone ring by oxidation of an enol silyl ether with 3-chloro-peroxybenzoic acid.

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