Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7

被引:57
|
作者
Manaviazar, Soraya [1 ]
Frigerio, Mark [1 ]
Bhatia, Gurpreet S. [1 ]
Hummersone, Marc G. [1 ]
Aliev, Abil E. [1 ]
Hale, Karl J. [1 ]
机构
[1] UCL, Ctr Chem Genom, Christopher Ingold Labs, Dept Chem, London WC1H 0AJ, England
关键词
D O I
10.1021/ol061626i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new enantioselective synthesis of Masamune's AB fragment (1) for bryostatin 7 is described. Key steps in the new route include a Meerwein-Ponndorf -Verley reduction to set the O(7) stereocenter and an alkylative union between the dithiane 6 and iodide 5 to construct the C(9) C(10) bond. Because we have previously published a synthesis of Masamune's C-ring phenyl sulfone 2, our new route to 1 constitutes a formal total synthesis of bryostatin 7; it also corrects the previously reported spectral data for 1 in CDCl3.
引用
收藏
页码:4477 / 4480
页数:4
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