Synlett 2014; 25(3): 303-307
DOI: 10.1055/s-0033-1340308
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© Georg Thieme Verlag Stuttgart · New York

New Strategies for Medium- and Large-Ring Lactone Synthesis

Wanxiang Zhao
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, P. R. of China   Fax: +852(2)3581594   Email: sunjw@ust.hk
,
Jianwei Sun*
Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, P. R. of China   Fax: +852(2)3581594   Email: sunjw@ust.hk
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Further Information

Publication History

Received: 25 September 2013

Accepted after revision: 28 October 2013

Publication Date:
06 December 2013 (online)

Abstract

Efficient synthesis of medium- and large-ring lactones is an important topic in organic synthesis. Summarized here are the conventional approaches and two recently reported new strategies. The both new intermolecular reactions employ siloxy alkynes as the key reaction partner. Enabled by the design of new (1,6)-amphoteric molecules and unprecedented ring expansion of fused oxetenium species, the two processes not only provide new solutions to medium- and large-ring lactone synthesis, but also overcome the drawbacks of traditional intramolecular cyclization strategies that typically require high dilution or slow addition.

 
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