6533b7d7fe1ef96bd1268d14
RESEARCH PRODUCT
Diastereoselective synthesis of spongian diterpenes. Total synthesis of the furanoditerpene (−)-spongia-13(16),14-diene
Manuel ArnóRamón J. ZaragozáMiguel A. Gonzalezsubject
DienebiologyStereochemistryOrganic ChemistryTotal synthesisRing (chemistry)biology.organism_classificationBiochemistrySpongiachemistry.chemical_compoundchemistryYield (chemistry)FuranIntramolecular forceDrug DiscoveryEnonedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1999-10-01 | Tetrahedron |