6533b7d2fe1ef96bd125e8e4

RESEARCH PRODUCT

Synthesis of spongian diterpenes: (−)-spongian-16-oxo-17-al and (−)-acetyldendrillol-1

Ramón J. ZaragozáManuel ArnóMiguel A. GonzálezM. Luisa Marin

subject

ChemistryStereochemistryOrganic ChemistryDrug DiscoveryAbsolute configurationSpongian-16-oxo-17-alBiochemistryAcetyldendrillol-1

description

Abstract An efficient diastereoselective synthesis of the spongian diterpenes (−)-spongian-16-oxo-17-al ( 1 ) and (−)-acetyldendrillol-1 ( 13 ) is described starting from (+)-podocarp-8(14)-13-one ( 6 ) via the ester-dialdehyde 11 as key intermediate. The absolute configuration at C-17 in synthetic compound 13 has conclusively been proved by NOE experiments.

https://doi.org/10.1016/s0040-4039(00)02339-x