Synthesis of the cyclobutanone core of solanoeclepin A via intramolecular allene butenolide photocycloaddition

Bui T. B. Hue; Jan Dijkink; Sanne Kuiper; Kimberly K. Larson; Frank S. Guziec, Jr.; Kees Goubitz; Jan Fraanje; Henk Schenk; Jan H. van Maarseveen; Henk Hiemstra

doi:10.1039/B311415E

Synthesis of the cyclobutanone core of solanoeclepin A via intramolecular allene butenolide photocycloaddition†

Bui T. B. Hue,^a Jan Dijkink,^a Sanne Kuiper,^a Kimberly K. Larson,‡^a Frank S. Guziec, Jr.,‡^a Kees Goubitz,^a Jan Fraanje,^a Henk Schenk,^a Jan H. van Maarseveen^a and Henk Hiemstra*^a

Author affiliations

* Corresponding authors

^a Institute of Molecular Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands
E-mail: hiemstra@science.uva.nl

Abstract

The compact tricyclic substructure of solanoeclepin A containing the cyclobutanone ring was prepared by using as the key step a highly regioselective intramolecular [2 + 2]-photocycloaddition reaction between one of the π-bonds of an allene and the CC double bond of a butenolide.

Organic & Biomolecular Chemistry

Synthesis of the cyclobutanone core of solanoeclepin A via intramolecular allene butenolide photocycloaddition†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Synthesis of the cyclobutanone core of solanoeclepin A via intramolecular allene butenolide photocycloaddition

Social activity

Search articles by author

Spotlight

Advertisements