Synthesis p. 426 - 427 (1989)
Update date:2022-09-26
Topics:
Zhou, Wei-Shan
Zhou, Yi-Pine
Jiang, Biao
Two brassinosteroids (stereoisomers of brassinolide), (22R,23R,24R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one (2) and (22S,23S,24R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one (3), were synthesized from ergosterol in eight steps in ca. 30percent overall yield.The key step is the highly regioselective formation of the 7-oxalactone ring by oxidation of an enol silyl ether with 3-chloroperoxybenzoic acid.
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Doi:10.1021/jo00077a047
(1993)Doi:10.1002/ardp.19903230912
(1990)Doi:10.1021/ja00248a048
(1987)Doi:10.1016/S0040-4039(01)93734-7
(1989)Doi:10.2478/s11532-009-0126-8
(2010)Doi:10.1021/ja1066465
(2010)
