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The first total synthesis of sporiolide A.

ABSTRACT: The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.

SUBMITTER: Du Y

PROVIDER: S-EPMC4140563 | biostudies-literature | 2006 Oct

REPOSITORIES: biostudies-literature

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The first total synthesis of sporiolide A.

Du Yuguo Y Chen Qi Q Linhardt Robert J RJ

The Journal of organic chemistry 20061001 22

The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound. ...[more]

PMID: 17064018

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