A general enantioselective approach to jasmonoid fragrances: synthesis of (+)-(1R,2S)-methyl dihydrojasmonate and (+)-(1R,2S)-magnolione

Alessio Porta; Giovanni Vidari; Giuseppe Zanoni

doi:10.1021/jo050423p

A general enantioselective approach to jasmonoid fragrances: synthesis of (+)-(1R,2S)-methyl dihydrojasmonate and (+)-(1R,2S)-magnolione

J Org Chem. 2005 Jun 10;70(12):4876-8. doi: 10.1021/jo050423p.

Authors

Alessio Porta¹, Giovanni Vidari, Giuseppe Zanoni

Affiliation

¹ Dipartimento di Chimica Organica, Università di Pavia, Viale Taramelli, 10-27100 Pavia, Italy.

PMID: 15932335
DOI: 10.1021/jo050423p

Abstract

Methyl dihydrojasmonate 1 and magnolione 3 are of both academic and industrial interest. In this paper, we describe a flexible, high-yielding route to diastereomerically pure (+)-cis-(1R,2S)-methyl dihydrojasmonate 1 and the first synthesis of (+)-cis-(1R,2S)-magnolione 3, both with enantiomeric excesses up to 93%. The two syntheses diverged from the same advanced intermediate 5, readily available from the enantioenriched hydroxymethyl delta-lactone (-)-(3aS,4S,6aR)-6. The olfactory properties of (1R,2S)-1 and (1R,2S)-3 are reported.

Publication types

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

MeSH terms

Catalysis
Cyclopentanes / chemical synthesis*
Cyclopentanes / chemistry
Molecular Structure
Perfume / chemical synthesis*
Perfume / chemistry
Stereoisomerism

Substances

Cyclopentanes
Perfume
magnolione
methyldihydrojasmonate