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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]

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