Synthesis of Tricyclic β-Methylene Spiro Lactones Related to Bakkenolides by Successive Radical Cyclization-High Pressure Diels-Alder Reactions

TG Back, PL Gladstone, M Parvez

文献索引：Back, Thomas G.; Gladstone, Patricia L.; Parvez, Masood Journal of Organic Chemistry, 1996 , vol. 61, # 11 p. 3806 - 3814

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被引用次数: 43

摘要

The synthesis of some novel bakkenolides and their epi-spiro analogues was achieved by a new approach. Photolysis of allyl 1-(phenylseleno)-2-oxocyclopentanecarboxylates 7-9 afforded the corresponding spiro lactones 10-12 by radical cyclization via group transfer of the phenylseleno group. Selenoxide elimination of 11 and 12 produced the corresponding β- methylene lactones 14 and 15. Diels-Alder cycloaddition of lactone 11 with piperylene ...