Synthesis 2002(14): 2150-2154
DOI: 10.1055/s-2002-34370
PAPER
© Georg Thieme Verlag Stuttgart · New York

Mechanistic Observations on the Unusual Reactivity of Dioxenone Photosubstrates­ in the Synthesis of Ingenol

Jeffrey D. Winkler*, Sean J. Harrison, Michael F. Greaney, Meagan B. Rouse
Department of Chemistry, The University of Pennsylvania, Philadelphia, PA 19104, USA
Fax: +1(215)5736329; e-Mail: winkler@sas.upenn.edu;
Further Information

Publication History

Received 14 August 2002
Publication Date:
26 September 2002 (online)

Abstract

The irradiation of allylically substituted dioxenone photosubstrates 6 and 21 lead to unexpected products, the formation of which can be explained by a series of transannular hydrogen atom abstractions.

1

Current address: Millennium Pharmaceuticals, Cambridge, MA, USA.

2

Current address: Department of Chemistry, University of Edinburgh, UK.