Total synthesis of mycalamide A.
Total synthesis of mycalamide A.
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DOI：
10.1021/ja050728l
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发表时间：
2005-05
影响因子：
15
通讯作者：
Jeong‐Hun Sohn;Nobuaki Waizumi;H. Zhong;V. Rawal
中科院分区：
文献类型：
--
作者：
Jeong‐Hun Sohn;Nobuaki Waizumi;H. Zhong;V. Rawal
本文报道了一种简洁有效的全合成方法-以（2 R，3R）-3-甲基-4-烯-2-醇为起始原料，经一步Pd（II）催化的串联Wacker/Heck环合反应制备四氢吡喃环系，经7步反应合成了左半部分（+）-7-苯甲酰基Pederic酸，总收率34.6%。右半部分，霉胺单元，由d-酒石酸二乙酯经21步合成，总收率为10.5%。开发了有效的立体选择性方法用于组装这两个部分以产生mycalamide A或C（10）-epi-mycalamide A。
This communication describes a concise and efficient total synthesis of mycalamide A by the convergent coupling of pederic acid unit with the mycalamine unit. The left-half, (+)-7-benzoylpederic acid, was synthesized from (2R,3R)-3-methylpent-4-en-2-ol in seven steps and 34.6% overall yield through a route that features a one-step Pd(II)-catalyzed tandem Wacker/Heck cyclization reaction to prepare the tetrahydropyran ring system. The right-half, the mycalamine unit, was synthesized in 21 steps and 10.5% overall yield from diethyl d-tartrate. Effective, stereoselective methods were developed for the assembly of the two parts to yield either mycalamide A or C(10)-epi-mycalamide A.