Jump to main content
Jump to site search

Issue 6, 2013
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Mar 2013, accepted on 11 Apr 2013 and first published on 15 Apr 2013


Article type: Edge Article
DOI: 10.1039/C3SC50643F
Chem. Sci., 2013,4, 2625-2629

  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements