An Efficient Formal Total Synthesis of (±-Stypoldione via Photochemically Triggered Biomimetic Cyclizations of Terpenoid Polyalkenes

Xuechao Xing; Martin Demuth

doi:10.1055/s-1999-3110

Synlett 1999; 1999(S1): 987-990
DOI: 10.1055/s-1999-3110

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An Efficient Formal Total Synthesis of (±-Stypoldione via Photochemically Triggered Biomimetic Cyclizations of Terpenoid Polyalkenes

Xuechao Xing^* , Martin Demuth

^*Max-Planck-Institut für Strahlenchemie, D-45413 Mühlheim an der Ruhr, Germany; Fax +49(2 08)3 06 39 51; E-mail: demuthm@mpi-muelheim.mpg.de

Abstract

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A novel and efficient synthesis of stypoldione, an antitumoral marine toxin, is accomplished by the application of photoinduced biomimetic cyclizations of terpenoid polyalkenes as the key step for the construction of the 6-6-6 tricyclic diterpene part of this natural product.

electron transfer - photochemistry - biomimetic radical cyclization - radical cation - (±)-stypoldione synthesis

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