The Journal of Organic Chemistry

Intramolecular [2+ 2] photochemical cycloadditions. 3. Perhydrohistrionicotoxin synthetic studies: synthesis of spiro [4.5] decanones via intramolecular [2+ 2] …

ER Koft, AB Smith III

文献索引：Koft, Emil R.; Smith, Amos B. Journal of Organic Chemistry, 1984 , vol. 49, p. 832 - 836

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被引用次数: 32

摘要

We describe here a full account of our efforts directed toward the synthesis of 4, a known intermediate in the synthesis of perhydrohistrionicotoxin (2). Irradiation of 7 followed by oxidative cleavage of the derived cyclobutene 6 produced 5 or 11, depending on the method of cyclobutene cleavage. While 5 could not be decarbonylated with (Ph3P) 3RhCl, thermal decarboxylation of 11 furnished 12a and 12b with the undesired stereochemistry at C (6) ...