Formal Synthesis of (±)-Platensimycin
- 1 April 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (9) , 1825-1828
- https://doi.org/10.1021/ol070563g
Abstract
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.Keywords
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