Stereochemistry of the Diels-Alder reaction of vinylcyclohexene or 1-[. alpha.-(tert-butyldimethylsilyloxy) vinyl]-. DELTA. 1-cyclohexene and 2-methylcyclopentenone

RE Ireland, WJ Thompson, NS Mandel…

Index: Ireland,R.E. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 20 p. 3583 - 3585

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Citation Number: 21

Abstract

As part of an investigation on the total synthesis of the macrolide antibiotic chlorothricolide,'an efficient synthesis of a cis-anti-trans fused tricyclic ring system such as I was required. A simple, convergent approach to the construction of such a tricyclic I might be the Diels-Alder reaction of a vinylcyclohexene (1) with 2-methylcyclopentenone (2).