TY - JOUR
T1 - α-Acylamino Radical Cyclizations
T2 - Application to the Synthesis of a Tetracyclic Substructure of Gelsemine
AU - Choi, Joong kwon
AU - Ha, Deok chan
AU - Hart, David J.
AU - Lee, Chih shone
AU - Ramesh, Subban
AU - Wu, Shung
PY - 1989/1/1
Y1 - 1989/1/1
N2 - Syntheses of gelsemine substructures 2 and 3 are described. Free-radical precursors 14,18, 35, and 38 were prepared, and their behavior upon treatment with tri-n-butyltin hydride and AIBN was examined. The radical derived from 14 afforded reduction product 15, whereas the radicals derived from 18, 35, and 38 gave cyclization products 23, 37, and 39, respectively. Aspects of these free-radical cyclizations as well as the conversion of 23 and 37 to 2 and 3, respectively, are presented.
AB - Syntheses of gelsemine substructures 2 and 3 are described. Free-radical precursors 14,18, 35, and 38 were prepared, and their behavior upon treatment with tri-n-butyltin hydride and AIBN was examined. The radical derived from 14 afforded reduction product 15, whereas the radicals derived from 18, 35, and 38 gave cyclization products 23, 37, and 39, respectively. Aspects of these free-radical cyclizations as well as the conversion of 23 and 37 to 2 and 3, respectively, are presented.
UR - http://www.scopus.com/inward/record.url?scp=0024502584&partnerID=8YFLogxK
U2 - 10.1021/jo00263a006
DO - 10.1021/jo00263a006
M3 - Article
AN - SCOPUS:0024502584
SN - 0022-3263
VL - 54
SP - 279
EP - 290
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 2
ER -