Total Synthesis of (±)-Stemodinone via an Efficient Ring-Exchange Strategy
The Journal of Organic Chemistry2001Vol. 66(21), pp. 7107–7112
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Tetsuaki Tanaka, Kazuo Murakami, Atsushi Kanda, Debasis Patra, Sachiko Yamamoto, Norifumi Satoh, Sangwon Kim, S. M. Abdur Rahman, Hiroaki Ohno, C. IWATA
Abstract
A total synthesis of (+/-)-stemodinone, a tetracyclic stemodane diterpene, from the known tricyclic methyl olefin 11 is described. The key steps involve an efficient ring-exchange reaction and palladium(0)-catalyzed lactone migration. The ring-exchange strategy for controlling the stereochemistry was based on an initial Diels-Alder reaction to form a new ring followed by cleavage of the original ring. Cleavage of the original ring of the Diels-Alder adduct 9 was achieved by an initial regio- and chemoselective Baeyer-Villiger oxidation followed by the Pd(0)-catalyzed lactone-migration reaction reported by us.
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