Enantioselective Total Synthesis of (+)-Psiguadial B
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- 作者：Lauren M. Chapman ; Jordan C. Beck ; Linglin Wu ; Sarah E. Reisman
- 刊名：Journal of the American Chemical Society
- 出版年：2016
- 出版时间：August 10, 2016
- 年：2016
- 卷：138
- 期：31
- 页码：9803-9806
- 全文大小：394K
- 年卷期：0
- ISSN：1520-5126
文摘
The first enantioselective total synthesis of the cytotoxic natural product (+)-psiguadial B is reported. Key features of the synthesis include (1) the enantioselective preparation of a key cyclobutane intermediate by a tandem Wolff rearrangement/asymmetric ketene addition, (2) a directed C(sp3)–H alkenylation reaction to strategically forge the C1–C2 bond, and (3) a ring-closing metathesis to build the bridging bicyclo[4.3.1]decane terpene framework.