General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form
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- 作者：Won-jin Chung ; Joseph S. Carlson ; Christopher D. Vanderwal
- 刊名：Journal of Organic Chemistry
- 出版年：2014
- 出版时间：March 7, 2014
- 年：2014
- 卷：79
- 期：5
- 页码：2226-2241
- 全文大小：875K
- 年卷期：v.79,no.5(March 7, 2014)
- ISSN：1520-6904
文摘
A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to 伪,尾-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and 11 steps, respectively.