Total Synthesis of (-)-Austalide B. A Generic Solution to Elaboration of the Pyran/p-Cresol/Butenolide Triad

LA Paquette, TZ Wang, MR Sivik

Index: Paquette, Leo A.; Wang, Ting-Zhong; Sivik, Matthew R. Journal of the American Chemical Society, 1994 , vol. 116, # 25 p. 11323 - 11334

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Citation Number: 26

Abstract

Abstract: The toxic meroterpenoid (-)-austalide B has been prepared in its natural form by chemical modification of the readily available optically active enedione 11. Following stereocontrolled Robinson annulation to give 13 and fully regiocontrolled gem-dimethylation of this intermediate, the highly functionalized tetracyclic ortho ester 22 was produced in four additional steps. At this point, it proved an easy matter to obtain 23 by Baeyer-Villiger ...

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