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Formal synthesis of (+/-)-platensimycin.

ABSTRACT: [reaction: see text] Reductive alkylation of 5-methoxy-1-tetralone (6) with 2,3-dibromopropene gave an equilibrium mixture of bicyclic diones 7 (51%) and 8 (35%). Radical cyclization of 7 afforded tricyclic dione 5 (84%), which was reduced, cyclized, and dehydrated to give tetracyclic alkene 13 in 63% yield. Allylic oxidation of 13 with SeO2 and activated MnO2 afforded enone 2 in 85% yield, thereby completing a short formal synthesis of (+/-)-platensimycin.

SUBMITTER: Zou Y

PROVIDER: S-EPMC2518405 | biostudies-literature | 2007 Apr

REPOSITORIES: biostudies-literature

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Formal synthesis of (+/-)-platensimycin.

Zou Yefen Y Chen Chun-Hsing CH Taylor Christopher D CD Foxman Bruce M BM Snider Barry B BB

Organic letters 20070404 9

[reaction: see text] Reductive alkylation of 5-methoxy-1-tetralone (6) with 2,3-dibromopropene gave an equilibrium mixture of bicyclic diones 7 (51%) and 8 (35%). Radical cyclization of 7 afforded tricyclic dione 5 (84%), which was reduced, cyclized, and dehydrated to give tetracyclic alkene 13 in 63% yield. Allylic oxidation of 13 with SeO2 and activated MnO2 afforded enone 2 in 85% yield, thereby completing a short formal synthesis of (+/-)-platensimycin. ...[more]

PMID: 17407302

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