Total Synthesis of Clerobungin A via a Cascade Cyclization Reaction
Total Synthesis of Clerobungin A via a Cascade Cyclization Reaction
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通过级联环化反应全合成 Clerobungin A
DOI：
10.1021/acs.joc.6b02261
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发表时间：
2016
期刊：
影响因子：
--
通讯作者：
Reber, Keith P.
中科院分区：
文献类型：
--
作者：
Mease, James;Reber, Keith P.
以市售酪醇为起始原料，经六步反应首次全合成了新的环己基乙醇类天然产物克拉邦金A，总收率14%。该序列中的关键步骤包括苯酚的生物启发氧化脱芳构化和半缩醛化/氧杂迈克尔级联以形成三环环系统。通过手性HPLC的后期中间体的分辨率允许用于两个对映体的氯邦吉A的手性光学性质的测量，支持天然产物的scalemic性质。
The first total synthesis of the novel cyclohexylethanoid natural product clerobungin A has been achieved in six steps and 14% overall yield starting from commercially available tyrosol. Key steps in this sequence include a bioinspired oxidative dearomatization of a phenol and a hemiacetalization/oxa-Michael cascade to form the tricyclic ring system. Resolution of a late-stage intermediate via chiral HPLC allowed for the measurement of the chiroptical properties of both enantiomers of clerobungin A, supporting the scalemic nature of the natural product.