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Synthesis of Angularly Fused Carbocycles via Tandem Radical Cyclization of α‐Carbonyl Radicals
Author(s) -
Prakash Chandran,
Mohanakrishnan Arasambattu K.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700986
Subject(s) - chemistry , tributyltin hydride , radical cyclization , radical , stereocenter , yield (engineering) , tandem , hydride , free radical reaction , tributyltin , carbonyl group , medicinal chemistry , stereochemistry , organic chemistry , enantioselective synthesis , catalysis , hydrogen , materials science , metallurgy , composite material
An α‐carbonyl radical cyclization approach towards the synthesis of angularly fused tricyclic systems is described. On reduction with tributyltin hydride, bromo ketones yield a α‐carbonyl radical that undergoes successive 5‐ exo‐dig / trig cyclizations, resulting in two or four contiguous stereocenters. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)