6533b821fe1ef96bd127ac15

RESEARCH PRODUCT

ChemInform Abstract: Diastereoselective Synthesis of Spongian Diterpenes. Total Synthesis of the Furanoditerpene (-)-Spongia-13(16),14-diene.

Miguel A. GonzalezRamón J. ZaragozáManuel Arnó

subject

biologyDieneStereochemistryTotal synthesisGeneral Medicinebiology.organism_classificationRing (chemistry)Spongiachemistry.chemical_compoundchemistryFuranIntramolecular forceYield (chemistry)Enone

description

Abstract An effective diastereoselective synthesis of the marine-sponge metabolite (−)-spongia-13(16),14-diene 1 is achieved starting from S-(+)-carvone via a homochiral phenanthrenone as the key intermediate for the construction of the furan ring system. S-(+)-Carvone was transformed into the phenanthrenone 2a in six steps (53% overall yield), using an intramolecular Diels-Alder reaction as the key step. Conversion of the enone function in 2a into an epoxyaldehyde function followed by cyclisation and aromatisation in acid conditions completed the construction of ring D.

yearjournalcountryeditionlanguage
2010-06-11ChemInform
https://doi.org/10.1002/chin.200003188