Concise formal synthesis of (+)-neopeltolide

Zhen Yang; Bingbin Zhang; Gaoyuan Zhao; Juan Yang; Xingang Xie; Xuegong She

doi:10.1021/ol2025718

Concise formal synthesis of (+)-neopeltolide

Org Lett. 2011 Nov 4;13(21):5916-9. doi: 10.1021/ol2025718. Epub 2011 Oct 13.

Authors

Zhen Yang¹, Bingbin Zhang, Gaoyuan Zhao, Juan Yang, Xingang Xie, Xuegong She

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.

PMID: 21995677
DOI: 10.1021/ol2025718

Abstract

A concise formal synthesis of (+)-neopeltolide (1) has been accomplished. The synthesis demonstrated high atom efficiency employing only one step of functional group protection. Key steps involved iridium-catalyzed double asymmetric carbonyl allylation, palladium-catalyzed intramolecular alkoxycarbonylation, ruthenium-catalyzed olefin isomerization, and ring-closing metathesis.

Publication types

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

MeSH terms

Macrolides / chemical synthesis*
Molecular Structure
Stereoisomerism

Substances

Macrolides
neopeltolide