6533b85efe1ef96bd12bfc6e

RESEARCH PRODUCT

First Diastereoselective Synthesis of (−)-Methyl Thyrsiflorin A, (−)-Methyl Thyrsiflorin B Acetate, and (−)-Thyrsiflorin C

Ramón J. ZaragozáManuel ArnóMiguel A. GonzálezAnd M. Luisa Marín

subject

Methyl thyrsiflorin B acetatePlants MedicinalMolecular StructureCyclopropanationSpectrum AnalysisOrganic ChemistryRegioselectivityStereoisomerismRing (chemistry)Cleavage (embryo)Medicinal chemistryCyclopropanechemistry.chemical_compoundThyrsiflorin CchemistryIntramolecular forceDiterpenes

description

An efficient procedure for the synthesis of scopadulan diterpenes, using (+)-podocarp-8(14)-en-13-one 13 as starting material, is reported. This procedure has been used for the diastereoselective synthesis of (-)-methyl thyrsiflorin A (8), (-)-methyl thyrsiflorin B acetate (9), and (-)-thyrsiflorin C (7). Key steps in our strategy are the intramolecular cyclopropanation of diazoketone 19 and the regioselective cleavage of the cyclopropane ring.

yearjournalcountryeditionlanguage
2000-05-18The Journal of Organic Chemistry
https://doi.org/10.1021/jo991561f