Vinylogous anionic processes in the formation and interconversion of tetracyclic ring systems?

Organic & Biomolecular Chemistry Pub Date: 2011-02-23 DOI: 10.1039/C0OB01152E

Abstract

Tandem oxy-Cope and transannular vinylogous aldol reactions and/or vinylogous retro-aldol, conjugate addition, and transannular vinylogous aldol reactions transformed some tricyclic vinyl enones into fused tetracycles under basic conditions. Mesylates derived from similar tetracyclic products underwent efficient skeletal reorganization via transannular ring-opening but then different modes of transannular ring-closure upon treatment with tert-butoxide.

Graphical abstract: Vinylogous anionic processes in the formation and interconversion of tetracyclic ring systems
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