Issue 19, 2001
From the journal:

Chemical Communications

An enantio- and stereocontrolled synthesis of (−)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis–Hillman reactionElectronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/cc/b1/b106471c/

Yoshiharu Iwabuchi,a   Mariko Furukawa,a   Tomoyuki Esumia  and  Susumi Hatakeyama*a  

* Corresponding authors

a Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki, Japan.
E-mail: susumi@net.nagasaki-u.ac.jp

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.

Graphical abstract: An enantio- and stereocontrolled synthesis of (−)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis–Hillman reaction

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Article information

DOI
https://doi.org/10.1039/B106471C
Article type
Communication
Submitted
01 Aug 2001
Accepted
29 Aug 2001
First published
18 Sep 2001

Chem. Commun., 2001, 2030-2031

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

Y. Iwabuchi, M. Furukawa, T. Esumi and S. Hatakeyama, Chem. Commun., 2001, 2030 DOI: 10.1039/B106471C

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