New ring conversion of monocyclic ketones to bicycloenone skeletons

Y Miyao, M Tanaka, H Suemune…

文献索引：Miyao, Yoshihiro; Tanaka, Masakazu; Suemune, Hiroshi; Sakai, Kiyoshi Journal of the Chemical Society, Chemical Communications, 1989 , # 20 p. 1535 - 1536

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被引用次数: 6

摘要

Previously, we have found that cyclopentanones or cyclohexanones with a carbonyl group in a side chain a- or p- to the ring carbonyl group readily undergo ring cleavage under acetalization conditions (BF3/ethylene glycol).2 We now report the novel conversion of cyclopentanones or cyclohex- anones with a carbonyl function at the 4- or 5-position of an a-side chain to bicycloenones. As shown in Table 1, substrates ... (6), and (7) under acetalization ...

~82%

~46%

~79%

Five-and six-membered-ring formation from olefinic. alpha.,....

[Stork,G.; Williard,P.G. Journal of the American Chemical Society, 1977 , vol. 99, p. 7067 - 7068]

The naturally occurring coumarins

[Bhandari, R. G.; Bhide, G. V. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983 , vol. 22, # 11 p. 1154 - 1155]

Sequential ene reactions-II: Synthesis of bicyclic adducts w...

[Snider, Barry B.; Goldman, Boris E Tetrahedron, 1986 , vol. 42, # 11 p. 2951 - 2956]

Total synthesis of (.+-.)-modhephene and its epimer,(.+-.)-e...

[Smith, Amos B.; Jerris, Paula J Journal of Organic Chemistry, 1982 , vol. 47, # 10 p. 1845 - 1855]

The naturally occurring coumarins

[Bhandari, R. G.; Bhide, G. V. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983 , vol. 22, # 11 p. 1154 - 1155]