RT Journal Article
T1 Stereoselective Synthesis of Hydrindane and Hydroazulene Derivatives by Transannular Cyclization of Nine- and Ten-Membered Carbocycles
A1 Martínez García, Lucas
A1 Prado, Gustavo
A1 Goñez, Karen V.
A1 Paleo Pillado, María Rita
A1 Sardina López, Francisco Javier
K1 Cyclization
K1 Layers
K1 Mixtures
K1 Organic compounds
K1 Solutions
AB Treatment of cis-fused bicyclic diene dicarboxylates with Li/naphthalene triggers a tandem ring-opening and transannular cyclization process that stereoselectively yields hydroazulenes and hydrindanes derivatives. Cyclononadienyl diesters, which can be isolated after the ring-opening step by judicious choice of the reaction conditions, undergo a tandem conjugate addition/intramolecular Michael addition upon treatment with chiral lithium amides to give bicyclic β-amino esters in a process where 4 contiguous stereocenters are formed with high diastereocontrol. A concise route toward the highly enantioenriched AEF ring core of the aconitine-type alkaloids has been developed as an application of this methodology. The starting cis-fused bicyclic dicarboxylates are easily prepared in one step by reductive alkylation of diisopropyl phthalate (Na/THF, followed by the appropriate bis-electrophiles).
PB The American Chemical Society
SN 0022-3263
YR 2021
FD 2021
LK http://hdl.handle.net/10347/32285
UL http://hdl.handle.net/10347/32285
LA eng
NO Martínez-García, L., Prado, G.  Góñez, K. V., Paleo, M.R., Sardina, F. J.(2021). Stereoselective Synthesis of Hydrindane and Hydroazulene Derivatives by Transannular Cyclization of Nine and Ten Membered Carbocycles. "Journal of Organic Chemistry",  vol. 86, n. 19, 13684–13692
NO This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright © 2021 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.1c01751.
NO Financial support from Ministerio de Economía y Competitividad of Spain (CTQ2017-84354-P), Xunta de Galicia (ED431C 2018/16 and Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G2019/03), and the European Regional Development Fund (ERDF) is gratefully acknowledged.
DS Minerva
RD 29 abr 2026