Abstract
A range of lactones and lactams have been successfully synthesized using atom transfer radical cyclisation (ATRC) reactions. In conjunction with Copper(I) chloride a diverse variety of heterocyclic systems have proved to be efficient catalyst systems. Copper(I)-4,4'-diheptyl-2,2'-bipyridine also facilitated the cyclisation of (2Z)-3,7-dimethyl-2,6-octadienyl-2,2,2-trichloroacetate, 1 to give a mixt. of diastereomeric bicyclic lactones, 2a, 2b. This tandem cyclisation has been used, in combination with a benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (Grubbs's 1st Generation) mediated ring closing metathesis reaction, to construct the tricyclic core found in eunicellin, 3, a biol. active mol. Grubbs's 1st Generation catalyst can be used to mediate ATRC reactions to yield lactones and lactams in good yields. Upon treating 2-cyclohexenyl 2,2,2-trichloroacetate, 4 with Grubbs' catalyst (3aS*,7aR*)-3,3-dichloro-2,3,3a,4,5,7a-hexahydrobenzo[b]furan-2-one, 5 was isolated in 75% yield and resulted from atom transfer cyclisation reaction followed by isomerisation of a double bond. Deuterated studies have shed light on the Gurjar mechanism for alkene isomerisation using Grubbs's olefin metathesis catalysts. [on SciFinder (R)]
| Original language | English |
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| Title of host publication | Abstracts of Papers, 227th ACS National Meeting, Anaheim, CA, United States, March 28-April 1, 2004 |
| Publication status | Published - 2004 |