An enantiocontrolled synthesis of a key intermediate to (+)-lactacystin

An enantiocontrolled synthesis of a key intermediate to (+)-lactacystin
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DOI:
10.1039/a804954h
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发表时间:
1998-09-21
影响因子:
4.9
通讯作者:
Jun, HS
Jun, HS
中科院分区:
化学2区
文献类型:
--
作者:
Kang, SH;Jun, HS

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从环氧化物2开始,通过分子内汞酰胺化三氯乙酸烯丙酯4,并同时用pr - 1 MgBr加成还原酯13,建立了关键中间体16到(+)-乳酸菌素1的不对称合成,其中中间体酮的还原具有完全的立体选择性。
An asymmetric synthesis of a key intermediate 16 to (+)-lactacystin 1 has been established starting from epoxide 2 via intramolecular mercurioamidation of allylic trichloroacetimidate 4 and concomitant addition-reduction of ester 13 by Pr-i MgBr, in which reduction of the intermediate ketone proceeded with complete stereoselectivity.