The Journal of Organic Chemistry

Intramolecular cobalt-mediated [2+ 2+ 2] cycloaddition of linear enediynes. A useful synthetic entry into cobalt-protected tricyclic dienes and their synthetic elaboration

ED Sternberg, KPC Vollhardt

Index: Sternberg, Ethan D.; Vollhardt, K. Peter C. Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1564 - 1573

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Citation Number: 42

Abstract

CpCo (CO), undergoes reaction with the linear a, b, w-enediynes 4, 10, 18, 22, and 25 to give the CpCo-complexed tricyclic dienes 5, 11, 19, 20, 23, 24, 26, and possibly 27. The free ligands may be obtained in good yield by oxidative demetalation. Treatment of the dienylsilane 12 with bromine gave the desilylated aromatic 13, whereas reaction with m- chloroperbenzoic acid furnished the dienol 14 and a-trimethylsilyl 0, y-enone 15. The ...