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Concise Total Synthesis of (±)-Deguelin and (±)-Tephrosin Using a Vinyl Iodide as a Key Building Block. | LitMetric
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Concise Total Synthesis of (±)-Deguelin and (±)-Tephrosin Using a Vinyl Iodide as a Key Building Block.

Shengtao Xu Guangyu Wang Feijie Xu Wenlong Li Aijun Lin Hequan Yao Jinyi Xu

J Nat Prod

State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry , China Pharmaceutical University, 24 Tong Jia Xiang , Nanjing 210009 , People's Republic of China.

Published: April 2018

A concise and protecting-group-free total synthesis of the antiproliferative natural product (±)-deguelin (2) was accomplished in four steps and 62% overall yield from commercially available precursors. The key transformation employed a vinyl iodide as the pivotal building block to construct the 4-acylchromene substructure present in deguelin. Subsequent CuO-mediated α-hydroxylation of deguelin (2) afforded tephrosin (3) in 90% yield.

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 Source
http://dx.doi.org/10.1021/acs.jnatprod.7b00794DOI Listing

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