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- Title
A Transannular Polyene Tetracyclization for Rapid Construction of the Pimarane Framework.
- Authors
Feilner, Julian M.; Wurst, Klaus; Magauer, Thomas
- Abstract
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.
- Subjects
CARBON-carbon bonds; ENOL ethers; CHEMICAL amplification; POLYENES; CONSTRUCTION
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 30, p12536
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202003127