Abstract:Der aus (‐)‐1‐Santonin (I) in literaturbekannter Weise zugängliche Ketoester (IIa) wird über (IIb) in den ungesättigten Ketoester (III) übergeführt, der bei der Bleitetraacetat‐Oxidation ein Gemisch aus (IV), (Va) und (Vb) gibt.
“…Oxidation of 13 with CrO 3 ·pyridine was slower but gave the same ratio of products. The formation of mixtures of products was expected because both ends of the intermediate allylic cation are secondary. 4 Allylic Oxidation of 13 to Give Enone 2 …”
[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.
“…Oxidation of 13 with CrO 3 ·pyridine was slower but gave the same ratio of products. The formation of mixtures of products was expected because both ends of the intermediate allylic cation are secondary. 4 Allylic Oxidation of 13 to Give Enone 2 …”
[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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