6533b827fe1ef96bd1286dbc

RESEARCH PRODUCT

Synthesis of elemane bis-lactones structurally related to vernolepin

Luz CardonaBegoña GarcíaGonzalo BlayJosé R. PedroLuisa Lahoz

subject

chemistry.chemical_classificationChemical transformationNatural productStereochemistryOrganic ChemistryNanotechnologyRing (chemistry)Biochemistrychemistry.chemical_compoundchemistryDrug DiscoveryVernolepinHemiacetalLactoneSantonin

description

Abstract The chemical transformation of santonin into an elemane bis -lactone structurally related to the antitumour compound vernolepin is reported. The transformation of ring A of santonin into a hemiacetal δ-lactone was achieved in eleven steps. The spectroscopic characteristics of the synthetic product obtained in this way revealed that the proposed structure for the natural product should be revised.

https://doi.org/10.1016/s0040-4039(98)00363-3