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

Xiangtao Chen; Lei Yu; Huijing Wang; Wen Zhang; Pei Tang; Fener Chen

doi:10.1039/d1cc04980a

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

Chem Commun (Camb). 2021 Nov 4;57(88):11669-11672. doi: 10.1039/d1cc04980a.

Authors

Xiangtao Chen¹, Lei Yu¹, Huijing Wang¹, Wen Zhang¹, Pei Tang¹, Fener Chen^{1

2

3}

Affiliations

¹ Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China. peitang@scu.edu.cn.
² Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China.
³ Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China.

PMID: 34672312
DOI: 10.1039/d1cc04980a

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.