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Enantioselective Synthesis of (-)-Acetylapoaranotin.

ABSTRACT: The first enantioselective total synthesis of the epipolythiodiketopiperazine (ETP) natural product (-)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (-)-emethallicin E and (-)-haemotocin are also achieved through the preparation of a symmetric cyclohexadienol-containing diketopiperazine.

SUBMITTER: Wang H

PROVIDER: S-EPMC5387676 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of (-)-Acetylapoaranotin.

Wang Haoxuan H Regan Clinton J CJ Codelli Julian A JA Romanato Paola P Puchlopek-Dermenci Angela L A AL Reisman Sarah E SE

Organic letters 20170328 7

The first enantioselective total synthesis of the epipolythiodiketopiperazine (ETP) natural product (-)-acetylapoaranotin (3) is reported. The concise synthesis was enabled by an eight-step synthesis of a key cyclohexadienol-containing amino ester building block. The absolute stereochemistry of both amino ester building blocks used in the synthesis is set through catalytic asymmetric (1,3)-dipolar cycloaddition reactions. The formal syntheses of (-)-emethallicin E and (-)-haemotocin are also ach ...[more]

PMID: 28349698

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