Total synthesis of (±)-flustramines A and C, (±)-flustramide A, and (-)- and (+)-debromoflustramines A
Total synthesis of (±)-flustramines A and C, (±)-flustramide A, and (-)- and (+)-debromoflustramines A
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DOI：
10.1021/jo800984a
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发表时间：
2008-08-01
影响因子：
3.6
通讯作者：
Sakamoto, Masanori
中科院分区：
文献类型：
--
作者：
Kawasaki, Tomomi;Shinada, Masashi;Sakamoto, Masanori
本文以吲哚啉-3-酮为起始原料，通过关键的多米诺反应，烯化-异构化-Claisen重排（OIC）和还原环化（RC），有效地全合成了三个标题六氢吡咯并[2，3-B]吲哚生物碱及其脱溴衍生物。以6-溴吲哚啉-3-酮9为起始原料，经关键中间体13 a，经5步反应合成了（+/-）-氟曲明C（5）。（+/-）-氟虫胺A（1）是由氟虫胺A（6）经五步还原制得。（+/-）-脱溴氟胺A（19）以类似的方式由13 b提供。用（R）-4-苯基恶唑烷-2-酮拆分（+/-）-羧酸17 b，合成了19的（-）-和（+）-对映体。
Here we describe the efficient total synthesis of the three title hexahydropyrrolo[2,3-b]indole alkaloids and debromo derivative from readily available indolin-3-ones using key domino reactions, olefination-isomerization-Claisen rearrangement (OIC), and reductive cyclization (RC). (+/-)-Flustramine C (5) was synthesized in five steps from 6-bromoindolin-3-one 9 via a key intermediate 13a. (+/-)-Flustramine A (1) has been obtained by reduction of flustramide A (6), which has been prepared in five steps from 13a. (+/-)-Debromoflustramine A (19) was provided in a similar manner from 13b. The (-)- and (+)-enantiomers of 19 were synthesized through optical resolution of (+/-)-carboxylic acid 17b using (R)-4-phenyloxazolidin-2-one.