Stereoselective total synthesis of (±)-vindeburnol and (±)-16-epi-vindeburnol

Abstract

A concise stereoselective total synthesis of (±)-vindeburnol and its epimer (±)-16-epi-vindeburnol is presented. This synthetic work features the utilization of Baeyer–Villiger oxidation to install different types of lactone substrate, and a sequence of aminolysis, aldimine condensation and acyl-Pictet–Spengler to deliver the crucial trans-fused indoloquinolizidine scaffold with high-level diastereocontrol.

Graphical abstract: Stereoselective total synthesis of (±)-vindeburnol and (±)-16-epi-vindeburnol

Supplementary files

Article information

Article type
Communication
Submitted
04 Sep 2021
Accepted
05 Oct 2021
First published
13 Oct 2021

Chem. Commun., 2021, Advance Article

Stereoselective total synthesis of (±)-vindeburnol and (±)-16-epi-vindeburnol

X. Chen, L. Yu, H. Wang, W. Zhang, P. Tang and F. Chen, Chem. Commun., 2021, Advance Article , DOI: 10.1039/D1CC04980A

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