An enantio- and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction

Y Iwabuchi; M Furukawa; T Esumi; S Hatakeyama

doi:10.1039/b106471c

An enantio- and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction

Chem Commun (Camb). 2001 Oct 7:(19):2030-1. doi: 10.1039/b106471c.

Authors

Y Iwabuchi¹, M Furukawa, T Esumi, S Hatakeyama

Affiliation

¹ Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.

PMID: 12240274
DOI: 10.1039/b106471c

Abstract

A new enantiocontrolled synthesis of a potent immunosuppressant(-)-mycestericin E has been accomplished by using cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction of an aldehyde with 1,1,1,3,3,3-hexafluoroisopropyl acrylate and Lewis acid-promoted cyclisation of an epoxytrichloroacetimidate as the key steps.

Publication types

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

MeSH terms

Acrylamide / chemistry*
Aldehydes / chemistry*
Catalysis
Cinchona Alkaloids / chemistry*
Fatty Acids, Monounsaturated / chemical synthesis*
Fatty Acids, Monounsaturated / chemistry
Kinetics
Magnetic Resonance Spectroscopy
Oxidation-Reduction
Plant Extracts
Stereoisomerism
Thermodynamics

Substances

Aldehydes
Cinchona Alkaloids
Fatty Acids, Monounsaturated
Plant Extracts
mycestericin D
Acrylamide