The Journal of Organic Chemistry

Total synthesis of halogenated monoterpene marine natural products via the Diels-Alder reaction

PG Williard, SE De Laszlo

Index: Williard, Paul G.; Laszlo, Stephen E. de Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3738 - 3749

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Citation Number: 21

Abstract

This work represents the first de novo synthetic approach to the halogenated, monocyclic monoterpenes isolated from red algae belonging to the genus Plocamium. The total syntheses of two natural products, ie, epi-plocamene D (2) and the allylic chloride 3, are presented along with an approach to the synthesis of violacene (1). A key step in the construction of the terpenoid skeleton is the Diels-Alder reaction utilizing a P-halogenated ...