Issue 6, 2015

Synthetic studies toward penitrem E: enantiocontrolled construction of B–E rings

Abstract

Enantiocontrolled construction of B–E rings of penitrem E was accomplished from 4-iodoindole in 13 steps with an overall yield of 1.7%. Diastereoselective Tf2NH-catalyzed (2+2)-cycloaddition between silyl enol ether and methyl acrylate furnished a tetracyclic product possessing the characteristic cyclobutane ring bearing a hydroxyl group.

Graphical abstract: Synthetic studies toward penitrem E: enantiocontrolled construction of B–E rings

Supplementary files

Article information

Article type
Communication
Submitted
28 Oct 2014
Accepted
19 Nov 2014
First published
21 Nov 2014

Chem. Commun., 2015,51, 1070-1073

Author version available

Synthetic studies toward penitrem E: enantiocontrolled construction of B–E rings

Y. Yoshii, T. Otsu, N. Hosokawa, K. Takasu, K. Okano and H. Tokuyama, Chem. Commun., 2015, 51, 1070 DOI: 10.1039/C4CC08505A

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