Total Synthesis of Principinol B
Qiang Du, Zhibo Fan, Ming Yang
Abstract
We have accomplished the first and asymmetric total synthesis of principinol B, a grayanoid possessing an oxabicyclo[3.2.1] architecture. A functionalized 5/7/6/5 tetracyclic intermediate was assembled in a convergent manner by a diastereoselective intermolecular aldol reaction and subsequent carbonyl-olefin metathesis of two enantiomerically enriched fragments. The oxabicyclo[3.2.1] architecture containing a 6,10-ether bridge was constructed by the Williamson ether synthesis.
Topics & Concepts
Total synthesisAldol reactionEtherOlefin metathesisMetathesisChemistryStereochemistryOlefin fiberIntermolecular forceSilyl etherMoleculeOrganic chemistrySilylationCatalysisPolymerizationPolymerBioactive Natural Diterpenoids ResearchSynthetic Organic Chemistry MethodsMarine Sponges and Natural Products