Formal synthesis of (+/-)-platensimycin.
[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.
Zou
Yefen
Y
Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Chen
Chun-Hsing
CH
Taylor
Christopher D
CD
Foxman
Bruce M
BM
Snider
Barry B
BB
D000218:Adamantane / Q000138:chemical synthesis* / Q000737:chemistry; D062365:Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry; D000813:Anilides / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014867:Water / Q000737:chemistry
D062365:Aminobenzoates; D000813:Anilides; D014867:Water; D000218:Adamantane; C510909:platensimycin