Premium
A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework
Author(s) -
Feilner Julian M.,
Wurst Klaus,
Magauer Thomas
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202003127
Subject(s) - polyene , chemistry , stereocenter , nucleophile , pyridazine , enol , enol ether , stereochemistry , ether , heteroatom , aryl , ring (chemistry) , diol , organic chemistry , enantioselective synthesis , alkyl , catalysis
Polyene cyclizations are one of the most powerful and fascinating chemical transformations to rapidly generate molecular complexity. However, cyclizations employing heteroatom‐substituted polyenes are rare. Described here is the tetracyclization of a dual nucleophilic aryl enol ether involving an unprecedented transannular endo ‐termination step. In this transformation, five stereocenters, two of which are quaternary, four carbon–carbon bonds, and four six‐membered rings are formed from a readily available cyclization precursor. The realization of this cyclization enabled short synthetic access to the tricyclic diterpenoid pimara‐15‐en‐3α‐8α‐diol.