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  • Concise total synthesis and stereochemical revision of (+)-naseseazines A and B: regioselective arylative dimerization of diketopiperazine alkaloids.

Concise total synthesis and stereochemical revision of (+)-naseseazines A and B: regioselective arylative dimerization of diketopiperazine alkaloids.

Journal of the American Chemical Society (2011-08-31)
Justin Kim, Mohammad Movassaghi
ABSTRACT

Concise and enantioselective total syntheses of (+)-naseseazines A and B are described. Our regioselective and directed dimerization of diketopiperazines provides their critical C3-C(sp(2)) linkages, an assembly with plausible biogenetic relevance. We revise the absolute stereochemistry of (+)-naseseazines A and B.

MATERIALS
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Sigma-Aldrich
(Isopropenyloxy)trimethylsilane, ≥85%