Synlett 2011(5): 722-724  
DOI: 10.1055/s-0030-1259677
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Studies toward the Total Synthesis of Chlorahololide A

Shan Qian, Gang Zhao*
Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Rd., Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: zhaog@mail.sioc.ac.cn;
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Publication History

Received 25 December 2010
Publication Date:
22 February 2011 (online)

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Abstract

The highly stereoselective synthesis of core framework 4, a pivotal intermediate for the total synthesis of chlorahololide A, is reported. The approach features t-BuCu-mediated stereoselective reduction of α,β-unsaturated diketone 8, Wharton transposition, Simmons-Smith cyclopropanation and cascade enol lactonization.