Journal of Organic Chemistry p. 6955 - 6964 (1994)
Update date:2022-08-03
Topics:
Lee, Jinhwa
Oh, Jonghoon
Jin, Shu-juan
Choi, Jong-Ryoo
Atwood, Jerry L.
Cha, Jin Kun
The azaallyl cation-mediated <4 + 3> cycloaddition with spiro<2.4>hepta-4,6-diene by the procedure of Schmid provides the tricyclic cycloadducts of general type 3.The keto bridge of the cycloadducts 17c, 21, and 22 has been cleaved by PhI(OAc)2-I2 (Suarez cleavage), which involves β-fragmentation of an alkoxy radical, to furnish iodo lactones 19, 32, and 30a,b, respectively.Subsequent oxidation of these alkyl iodides has been investigated to develop a new synthetic route for bridgehead olefins (i.e., 33) of medium-sized carbocycles.
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