Enantioselective and collective syntheses of xanthanolides involving a controllable dyotropic rearrangement of cis-β-lactones

Weiwu Ren; Yichao Bian; Ziyang Zhang; Hai Shang; Pengtao Zhang; Yuejie Chen; Zhen Yang; Tuoping Luo; Yefeng Tang

doi:10.1002/anie.201202643

Enantioselective and collective syntheses of xanthanolides involving a controllable dyotropic rearrangement of cis-β-lactones

Angew Chem Int Ed Engl. 2012 Jul 9;51(28):6984-8. doi: 10.1002/anie.201202643. Epub 2012 Jun 4.

Authors

Weiwu Ren¹, Yichao Bian, Ziyang Zhang, Hai Shang, Pengtao Zhang, Yuejie Chen, Zhen Yang, Tuoping Luo, Yefeng Tang

Affiliation

¹ The Comprehensive AIDS Research Center, Department of Pharmacology & Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, China.

PMID: 22674838
DOI: 10.1002/anie.201202643

Abstract

Let's swap: a scalable, atom-economic, enantio-, and diastereoselective synthetic route to trisubstituted γ-butyrolactones based on a Wagner-Meerwein-type dyotropic rearrangement of cis-β-lactones is described. This methodology was applied in efficient and protecting-group-free formal syntheses and total syntheses of various xanthanolide natural products.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

4-Butyrolactone / chemistry*
Biological Products / chemical synthesis*
Lactones / chemistry*
Molecular Structure
Sesquiterpenes / chemical synthesis*
Stereoisomerism
Xanthium / chemistry*

Substances

Biological Products
Lactones
Sesquiterpenes
4-Butyrolactone