Total Synthesis of (−)-Enigmazole A by the Macrocyclization/Transannular Pyran Cyclization Strategy
Taisei Masuda, Kyoya Ohyama, Atsushi Yoshimura, Haruhiko Fuwa
Abstract
An 18-step synthesis of (−)-enigmazole A is herein disclosed. The present synthesis is based on a modular assembly of three building blocks of similar complexity, a macrocyclic ring-closing metathesis to forge the 18-membered macrocyclic skeleton, and a desilylative transannular oxa-Michael addition for stereoselective construction of the 2,6- cis -substituted tetrahydropyran ring.
Topics & Concepts
ChemistryTetrahydropyranPyranStereoselectivityRing (chemistry)StereochemistryRing-closing metathesisMetathesisSalt metathesis reactionCombinatorial chemistryOrganic chemistryCatalysisPolymerPolymerizationSynthetic Organic Chemistry MethodsChemical Synthesis and AnalysisMarine Toxins and Detection Methods