Convergent biomimetic semisynthesis of disesquiterpenoid rumphellolide J
Georgijs Stakanovs, Sergey Belyakov, Aigars Jirgensons, Dace Rasiņa
Abstract
acyl fluoride and alkoxide of 4β,8β-epoxycaryophyllan-5-ol gave rumphellolide J in 70% yield (1.65 g). The same structure for the synthesized product and natural isolate was proven despite the opposite specific rotation value of the intermediate acid. The short access to the terpenoids provides a material for further investigations of biological activities and valuable reference standards for the analysis of the chemical composition of various natural sources.
Topics & Concepts
SemisynthesisChemistryBiochemical engineeringStereochemistryEngineeringSynthetic Organic Chemistry MethodsSesquiterpenes and Asteraceae StudiesMarine Sponges and Natural Products