TY - JOUR
T1 - A Method to Access Highly Functionalized Dibenzobicyclo[3.2.1]octadienones
T2 - Application to the Construction of the 6/6/5/6/6 Carbon Skeleton of Rubialatin A
AU - Hazra, Gurupada
AU - Mishra, Gitanjali
AU - Dandela, Rambabu
AU - Thirupathi, Barla
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/9/16
Y1 - 2022/9/16
N2 - The dibenzobicyclo[3.2.1]octadienone scaffold, which has been found in naphthocyclinones, engelharquinones, rubialatin A, etc., has been synthesized under mild transition metal-free conditions by aryne insertion reaction with 2-keto-1,3-indandiones. The application of this methodology has been demonstrated for the synthesis of the 6/6/5/6/6 scaffold of rubialatin A. 1H NMR experimental studies confirm that the reaction proceeds through the formation of benzocyclobutane followed by a 7-member carbocycle ring.
AB - The dibenzobicyclo[3.2.1]octadienone scaffold, which has been found in naphthocyclinones, engelharquinones, rubialatin A, etc., has been synthesized under mild transition metal-free conditions by aryne insertion reaction with 2-keto-1,3-indandiones. The application of this methodology has been demonstrated for the synthesis of the 6/6/5/6/6 scaffold of rubialatin A. 1H NMR experimental studies confirm that the reaction proceeds through the formation of benzocyclobutane followed by a 7-member carbocycle ring.
UR - http://www.scopus.com/inward/record.url?scp=85129193194&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.2c00340
DO - 10.1021/acs.joc.2c00340
M3 - Article
AN - SCOPUS:85129193194
SN - 0022-3263
VL - 87
SP - 11925
EP - 11938
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -