RADICAL MEDIATED CYCLIZATION REACTIONS

  • Feldman, Ken S. (PI)

Project: Research project

Project Details

Description

Many therapeutically important natural products and pharmaceutical agents
can be prepared from functionalized cyclopentane and dioxolane derivatives.
The continued development of methodology for the efficient and
stereoselective synthesis of these ring systems is proposed. This
methodology is based on the free radical mediated addition of
functionalized olefins or related species across the carbon-carbon bond of
suitably activated vinylcyclopropanes to afford directly the cyclopentane
units. Emphasis is placed on enhancing current levels of dia-
stereoselectivity and enantioselectivity upon bond formation. Further, the
development of novel free radical-based annelation/isomerization reactions
for the construction of highly functionalized cyclopentanol species is
planned. Finally, diastereoselective remote (Gamma) functionalization of
secondary alcohols will be explored.

Syntheses of the antitumor antibiotic brefeldin A and The antileukemic
agent rocaglamide, which each utilize intramolecular variants of the cyclo-
pentannelation process, will be investigated. Successful completion of
these syntheses will afford the targets (or analogs) in the most efficient
manner to date.
StatusFinished
Effective start/end date7/1/926/30/93

Funding

  • National Institute of General Medical Sciences

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