Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin

O Dirat; C Kouklovsky; Y Langlois

doi:10.1021/ol990734k

Oxazoline N-oxide-mediated [2+3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin

Org Lett. 1999 Sep 9;1(5):753-5. doi: 10.1021/ol990734k.

Authors

O Dirat¹, C Kouklovsky, Y Langlois

Affiliation

¹ Laboratoire de Synthèse des Substances Naturelles, Associé au CNRS, ICMO, Bâtiment 410, Université de Paris-sud, 91405 Orsay, France.

PMID: 16118878
DOI: 10.1021/ol990734k

Abstract

[reaction: see text] A [2+3] cycloaddition of camphor-derived oxazoline N-oxide to alpha,beta-unsaturated ester afforded adduct 8. Tetrahydrolipstatin 1 was prepared from this compound in a nine-step sequence of reactions.

Publication types

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

MeSH terms

Aldehydes
Cyclization
Hydrolysis
Indicators and Reagents
Lactones / chemical synthesis*
Magnetic Resonance Spectroscopy
Orlistat
Oxazoles / chemistry*
Oxidation-Reduction

Substances

Aldehydes
Indicators and Reagents
Lactones
Oxazoles
Orlistat