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Issue 1, 2015
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A catalytic asymmetric total synthesis of (−)-perophoramidine

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Abstract

We report a catalytic asymmetric total synthesis of the ascidian natural product perophoramidine. The synthesis employs a molybdenum-catalyzed asymmetric allylic alkylation of an oxindole nucleophile and a monosubstituted allylic electrophile as a key asymmetric step. The enantioenriched oxindole product from this transformation contains vicinal quaternary and tertiary stereocenters, and is obtained in high yield along with high levels of regio-, diastereo-, and enantioselectivity. To install the second quaternary stereocenter in the target, the route utilizes a novel regio- and diastereoselective allylation of a cyclic imino ether to deliver an allylated imino ether product in near quantitative yield and with complete regio- and diastereocontrol. Oxidative cleavage and reductive amination are used as final steps to access the natural product.

Graphical abstract: A catalytic asymmetric total synthesis of (−)-perophoramidine

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Supplementary files

Article information


Submitted
19 Jun 2014
Accepted
30 Jul 2014
First published
30 Jul 2014

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2015,6, 349-353
Article type
Edge Article
Author version available

A catalytic asymmetric total synthesis of (−)-perophoramidine

B. M. Trost, M. Osipov, S. Krüger and Y. Zhang, Chem. Sci., 2015, 6, 349
DOI: 10.1039/C4SC01826E

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