A Synthetic Approach for Constructing the 3/6/6/5‐Fused Tetracyclic Skeleton of Tenuipesine A |
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| Authors: | Jin‐Miao Tian Dr Xiong Zhao Prof?Dr Yong‐Qiang Tu Wei Gong Prof?Dr Fu‐Min Zhang Dr Shu‐Yu Zhang Prof?Dr Shao‐Hua Wang |
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| Institution: | 1. State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 (P. R. China);2. School of Pharmacy, Lanzhou University, Lanzhou, 730000 (P. R. China) |
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| Abstract: | An efficient approach toward the 3/6/6/5‐fused tetracyclic skeleton of tenuipesine A has been accomplished. The strategy featured 1) a tandem Mitsunobu and 3,3‐rearrangement reaction yielding the key intermediate 7 with two adjacent all‐carbon quaternary centers with high d.r.; and 2) a tandem DBDMH‐mediated semipinacol rearrangement via a 1,2‐oxygen migration of an allylic hemiketal to construct the highly substituted tetrahydropyran ring. |
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| Keywords: | Mitsunobu reaction rearrangement semipinacol synthesis tenuipesine A |
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