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Formal synthesis of (+/-)-platensimycin
Yefen Zou1, Chun-Hsing Chen, Christopher D Taylor
1Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
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.
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