Journal of Organic Chemistry p. 3960 - 3964 (1982)
Update date:2022-08-02
Topics:
Taylor, Michael D.
Minaskanian, Gevork
Winzenberg, Kevin N.
Santone, Particia
Smith, Amos B.
A potentially versatile intermediate for the synthesis of natural products containing the bicyclo<5.1.0>octane ring system is 8,8-dimethylbicyclo<5.1.0>oct-2-en-4-one (1).This intermediate was prepared efficiently in racemic form from 5-acetoxycycloheptene and in chiral form (1R,7S) from (-)-2-carene, via separate synthetic strategies.In addition, a number of 4-hydroxy(acetoxy)bicyclo<5.1.0>octanes (3, 4, and 6) were also prepared and their stereochemistry established rigorously by NMR spectroscopy and chemical correlation to 3t, the structure of which was determined by X-ray crystallographic analysis.
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Doi:10.1021/ja01214a060
(1946)Doi:10.1002/cber.19821150708
(1982)Doi:10.1021/jm00362a020
(1983)Doi:10.1080/00397919508015425
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(1982)