Issue 6, 2013

Synthesis of cyclobutanelignansvia an organic single electron oxidant–electron relay system

Abstract

A direct method to synthesize lignan cyclobutanes and analogs via photoinduced electron transfer is presented. A variety of oxygenated alkenes are employed to furnish terminal or substituted cyclobutane adducts with complete regiocontrol, yielding cycloadducts with trans stereochemistry. Key to minimizing competing cycloreversion is the inclusion of an aromatic electron relay (ER). This method has been adapted to the synthesis of the natural products magnosalin and pellucidin A.

Graphical abstract: Synthesis of cyclobutane lignans via an organic single electron oxidant–electron relay system

Supplementary files

Article information

Article type
Edge Article
Submitted
07 Mar 2013
Accepted
11 Apr 2013
First published
15 Apr 2013

Chem. Sci., 2013,4, 2625-2629

Synthesis of cyclobutane lignans via an organic single electron oxidant–electron relay system

M. Riener and D. A. Nicewicz, Chem. Sci., 2013, 4, 2625 DOI: 10.1039/C3SC50643F

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