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Synthesis of a ketone analogue of biotin via the intramolecular Pauson-Khand reaction.

ABSTRACT: We report an improved synthesis of 5-(5-oxohexahydrocyclopenta[c]thiophen-1-yl)pentanoic acid (ketone biotin, 1) based on the intramolecular Pauson-Khand cyclization. The synthesis proceeds in eight steps and in 2.7% overall yield from cyclohexene.

SUBMITTER: McNeill E 

PROVIDER: S-EPMC2531226 | biostudies-literature | 2006 Sep

REPOSITORIES: biostudies-literature

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Synthesis of a ketone analogue of biotin via the intramolecular Pauson-Khand reaction.

McNeill Eric E   Chen Irwin I   Ting Alice Y AY  

Organic letters 20060901 20

We report an improved synthesis of 5-(5-oxohexahydrocyclopenta[c]thiophen-1-yl)pentanoic acid (ketone biotin, 1) based on the intramolecular Pauson-Khand cyclization. The synthesis proceeds in eight steps and in 2.7% overall yield from cyclohexene. ...[more]

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