Synthesis of Isopulo'upone

Jorma Matikainen Division of Organic Chemistry, Department of Chemistry, University of Helsinki, Vuorikatu 20, SF-00100, Helsinki, Finland

Seppo Kaltia Division of Organic Chemistry, Department of Chemistry, University of Helsinki, Vuorikatu 20, SF-00100, Helsinki, Finland

Tapio Hase Division of Organic Chemistry, Department of Chemistry, University of Helsinki, Vuorikatu 20, SF-00100, Helsinki, Finland

Abstract

Two routes are reported for the synthesis of the title marine metabolite 1. The routes converge at the trienoic aldehyde 4, and are completed by chain extension to the tetraenoic ketone 5 and intramolecular Diels-Alder cyclization. - Daylight lamp irradiation offers a convenient means for converting a cis/trans mixture from a Wittig reaction into the pure trans isomer.

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Synthesis of Isopulo'upone

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Synthesis of Isopulo'upone

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