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Total synthesis of (+/-)-aplykurodinone-1: traceless stereochemical guidance.

ABSTRACT: The total synthesis of the highly degraded steroidal natural product, aplykurodinone-1 (1), has been accomplished. Key features include a one-flask hydrolysis/retro-aldol/iodolactonization sequence to excise the C(8) hydroxymethylene functionality with retention of stereochemistry and the stereoselective installation of the C(13) methyl group through hydrogenation with homogeneous catalyst.

SUBMITTER: Zhang Y

PROVIDER: S-EPMC2912429 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Total synthesis of (+/-)-aplykurodinone-1: traceless stereochemical guidance.

Zhang Yandong Y Danishefsky Samuel J SJ

Journal of the American Chemical Society 20100701 28

The total synthesis of the highly degraded steroidal natural product, aplykurodinone-1 (1), has been accomplished. Key features include a one-flask hydrolysis/retro-aldol/iodolactonization sequence to excise the C(8) hydroxymethylene functionality with retention of stereochemistry and the stereoselective installation of the C(13) methyl group through hydrogenation with homogeneous catalyst. ...[more]

PMID: 20513158

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