Total synthesis of (±)-spiniferin-1 via a polyfluoroalkanosulfonyl fluoride induced homoallylic carbocation rearrangement reaction

Kai Ding; Yun-Shan Sun; Wei-Sheng Tian

doi:10.1021/jo102351k

Total synthesis of (±)-spiniferin-1 via a polyfluoroalkanosulfonyl fluoride induced homoallylic carbocation rearrangement reaction

J Org Chem. 2011 Mar 4;76(5):1495-8. doi: 10.1021/jo102351k. Epub 2011 Jan 20.

Authors

Kai Ding¹, Yun-Shan Sun, Wei-Sheng Tian

Affiliation

¹ Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, China.

PMID: 21250703
DOI: 10.1021/jo102351k

Abstract

A facile total synthesis of marine natural product (±)-spiniferin-1 has been accomplished in eight steps with 28.9% overall yield, involving a rearrangement reaction initiated by polyfluoroalkanosulfonyl fluoride to construct the 1,6-methano[10]annulene core of the natural product as a key step.

Publication types

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

MeSH terms

Heterocyclic Compounds, 3-Ring / chemical synthesis*
Heterocyclic Compounds, 3-Ring / chemistry
Hydrocarbons, Fluorinated / chemistry*
Molecular Structure
Stereoisomerism

Substances

Heterocyclic Compounds, 3-Ring
Hydrocarbons, Fluorinated
spiniferin-1