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Synthesis of Azabicyclic Building Blocks for Daphniphyllum Alkaloid Intermediates Featuring N ‐Trichloroacetyl Enamide 5‐ endo ‐ trig Radical Cyclizations
Author(s) -
Jansana Sergi,
Coussanes Guilhem,
Puig Jordi,
Diaba Faiza,
Bonjoch Josep
Publication year - 2019
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201900188
Subject(s) - chemistry , stereocenter , radical cyclization , ring (chemistry) , stereochemistry , derivative (finance) , alkaloid , total synthesis , enantioselective synthesis , organic chemistry , financial economics , economics , catalysis
A general procedure is reported for the synthesis of cis ring fused azapolycyclic compounds bearing an all‐carbon quaternary stereocenter at the ring fusion and an adequate functionalization for the assembly of new rings leading to advanced synthetic intermediates for Daphniphyllum alkaloid synthesis. The key carbon−carbon bond‐forming step in this approach is a radical cyclization of an N ‐cycloalkenyl trichloroacetamide derivative involving a tetrasubstituted enamide to achieve polyfunctionalized lactams.