Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide.: Part 1:: Synthetic strategy and preparation of a common precursor
Large-scale synthesis of the anti-cancer marine natural product (+)-discodermolide.: Part 1:: Synthetic strategy and preparation of a common precursor
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DOI：
10.1021/op034130e
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发表时间：
2004-01-01
影响因子：
3.4
通讯作者：
Gamboni, R
中科院分区：
文献类型：
--
作者：
Mickel, SJ;Sedelmeier, GH;Gamboni, R
描述了使用混合Novartis-Smith-Paterson合成路线通过共同前体3生产多克量的（+）-discodermolide（1）的合成策略。在这个五部分系列的第一部分，我们提出了一个数公斤的制备α-甲基醛10从罗氏酯，其syn-aldol反应与埃文斯硼烯醇化物，去除手性助剂，和Weinreb酰胺3（史密斯共同前体）的制备。共同的前体在没有任何色谱的情况下产生。
The synthetic strategy for producing multigram quantities of (+)-discodermolide (1) using a hybridized Novartis-Smith-Paterson synthetic route via common precursor 3 is described. In the first part of this five-part series, we present a multikilogram preparation of alpha-methyl aldehyde 10 from Roche ester, its syn-aldol reaction with Evans boron enolate, removal of the chiral auxiliary, and the preparation of Weinreb amide 3 (Smith common precursor). The common precursor was produced without any chromatography.