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Pd‐Catalyzed Regio‐ and Diastereoselective Heck Cyclization to Access Bicyclo[3.2.1]octanone Ring Systems
Author(s) -
Li Bo,
Zhang Guiming,
Xu Tao
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202001089
Subject(s) - bicyclic molecule , chemistry , regioselectivity , alkyne , ring (chemistry) , alkene , catalysis , reagent , radical cyclization , octene , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , ethylene
Bridged‐ring systems, especially the bicyclo[3.2.1]octanes, are widely found as key structural motifs in 6,7‐ seco‐ent ‐kaurane diterpenoids. In an effort directed towards the total synthesis of sculponeatin N, a Pd‐catalyzed regioselective reductive‐Heck cyclization was developed to access variously substituted bicyclo[3.2.1]octan‐2‐ones, with isolated yields up to 94 %, starting from commercially available anisole derivatives. The reactions displayed complementary merits to classical radical‐mediated pathway in both avoiding stoichiometric tin reagent and good compatibility towards alkyne/alkene bearing substrates.