1. An Efficient Synthesis of a Cyclopentannulated Pyrrolidine Derivative.
- Author
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Khan, Faiz Ahmed and Upadhyay, Sarasij K.
- Subjects
- *
ORGANIC synthesis research , *PYRROLIDINE , *HYDROGEN peroxide , *OXIDATION-reduction reaction , *DIELS-Alder reaction , *CHEMICAL reactions , *HALOGENATION - Abstract
A racemic cyclopentannulated pyrrolidine derivative was synthesized utilizing ruthenium oxidation and borane reduction as the key steps. Ruthenium oxidation reaction of the 1,2-dibromoalkene moiety in an N-Boc-protected tetrabromonorbornyl derivative afforded a tricyclic α-hydroxy ketone, which on alkaline hydrogen peroxide cleavage furnished a bicyclic lactam in excellent yield. Borane reduction of the N-Boc-protected bicyclic lactam gave an unexpected product as a single diastereomer resulting from the reduction of not only the lactam and ester moieties but also the ketal to the corresponding methyl ether. A plausible mechanism involving an oxocarbenium ion is discussed. [ABSTRACT FROM AUTHOR]
- Published
- 2011
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