Ring scission of diastereomeric 4-butylspiropentylcarbinyl radicals as a chemical model for identifying enzyme-catalyzed FAD adducts resulting from spiropentylacetyl …

L Lis, ES Koltun, H Liu, SR Kass

Index: Lis, Lev; Koltun, Elena S.; Liu, Hung-Wen; Kass, Steven R. Journal of the American Chemical Society, 2002 , vol. 124, # 7 p. 1276 - 1287

Full Text: HTML

Citation Number: 6

Abstract

Both diastereomeric 4-butylspiropentylcarbinyl bromides (14a and 14b) were synthesized in seven steps starting from 1-heptyne, and the stereochemical assignments based upon NOE experiments were confirmed by converting their immediate alcohol precursors (13a and 13b) to 1, 4-dibutylspiropentanes (17a and 17b) with C 1 and C 2 symmetry. Each bromide was used to generate its corresponding spiropentylcarbinyl radical (18a and 18b) via its ...