Facile Syntheses of Brassinosteroids: Brassinolide, Castasterone, Teasterone and Typhasterol
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概要
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(22R, 23R, 24S)-3α, 5-Cyclo-22, 23-diacetoxy-5α-ergostan-6-one (2b) is a new key intermediate of some naturally occurring brassinosteroids such as brassinolide (1a), castasterone (1b), teasterone (1c) and typhasterol (1d). The cycloketone 2b was prepared in 10 steps via (22R, 23R, 24S)-6β-benzyloxy-3a, 5-cyclo-22, 23-dihydroxy-5α-ergostane (5) from stigmasterol. 2b was treated with a catalytic amount of p-toluenesulfonic acid and sodium bromide to give an enone (7b), which was oxidized with osmium tetroxide and derived to give a 2α, 3α-acetonide (8b). 8b was easily separated from its isomer by the use of silica gel column chromatography. 8b was oxidized with trifluoroperacetic acid and deacetylated to give 1a. 8b was deacetylated and deacetonized to give 1b. 2b was treated with dilute sulfuric acid in acetic acid to give a 3β-acetate (10). 10 was treated with sodium hydroxide to give 1c. 2b was treated with hydrobromic acid to give a 3β-bromide (12), which was treated with silver acetate to give a 3α-acetate (13). 13 was treated with sodium hydroxide to give 1d.
- 社団法人 日本農芸化学会の論文
著者
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TAKEUCHI Tadashi
Research Division, Fuji Chemical Industries Ltd.
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Aburatani Masakazu
Research Division Fuji Chemical Industries Ltd.
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Takeuchi Tadashi
Research Division Fuji Chemical Industries Ltd.
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Mori Kenji
Department Of Agricultural Chemistry College Of Science And Technology The University Of Tokyo
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