Synthesis of (+)-spirolaxine methyl ether

Raffaella Nannei; Sabrina Dallavalle; Lucio Merlini; Adriana Bava; Gianluca Nasini

doi:10.1021/jo060839i

Synthesis of (+)-spirolaxine methyl ether

J Org Chem. 2006 Aug 4;71(16):6277-80. doi: 10.1021/jo060839i.

Authors

Raffaella Nannei¹, Sabrina Dallavalle, Lucio Merlini, Adriana Bava, Gianluca Nasini

Affiliation

¹ Dipartimento di Scienze Molecolari Agroalimentari, Università di Milano, Via Celoria 2, 20133 Milano, Italy.

PMID: 16872220
DOI: 10.1021/jo060839i

Abstract

A short and efficient synthesis of (+)-spirolaxine methyl ether, a metabolite of the fungus Sporotrichum laxum with inhibitory activity against Helicobacter pylori, is described. The synthesis has been carried out by a Prins cyclization, to obtain the [6,5]-spiroketal system, and a Wadsworth-Emmons condensation, applied for the installation of the polymethylene chain on the phthalide moiety.

Publication types

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

MeSH terms

Magnetic Resonance Spectroscopy
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry

Substances

Spiro Compounds
spirolaxine methyl ether