Issue 10, 2014

A rapid and efficient access to renieramycin-type alkaloids featuring a temperature-dependent stereoselective cyclization

Abstract

A flexible and practical protocol for the asymmetric synthesis of renieramycin-type antitumor alkaloids is described, in which the stereoselective Pictet–Spengler cyclization of amino ester 16 and aldehyde 15 by regulating temperature and the automatic lactamization after N-deprotection of the cyclization product are exploited to rapidly construct the common pentacyclic framework. (–)-Renieramycin G and (–)-jorunnamycin A, as representative members of the two subgroup renieramycin-type alkaloids, are obtained in 19 steps from L-tyrosine with 15.8% and 14.3% overall yield respectively.

Graphical abstract: A rapid and efficient access to renieramycin-type alkaloids featuring a temperature-dependent stereoselective cyclization

Supplementary files

Article information

Article type
Paper
Submitted
08 Nov 2013
Accepted
30 Dec 2013
First published
06 Jan 2014

Org. Biomol. Chem., 2014,12, 1633-1640

A rapid and efficient access to renieramycin-type alkaloids featuring a temperature-dependent stereoselective cyclization

H. Liu, R. Chen and X. Chen, Org. Biomol. Chem., 2014, 12, 1633 DOI: 10.1039/C3OB42209G

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