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Total syntheses of (±)-musellarins A-C
Zhilong Li1, Tsz-Fai Leung, Rongbiao Tong
1Department of Chemistry, The Hong Kong University of Science and Technology, Clearwater Bay, Kowloon, Hong Kong, China. rtong@ust.hk.
Abstract:
The first, diastereoselective total syntheses of musellarins A-C were achieved concisely with 7.8-9.8% yields in 15-16 steps. The key synthetic features include (i) an Achmatowicz rearrangement, Kishi reduction, and Friedel-Crafts cyclization to construct the tricyclic framework and (ii) Heck coupling of aryldiazonium salts to introduce the aryl group into the dihydropyran in a 2,6-trans fashion in the final stage of synthesis.
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