6533b871fe1ef96bd12d0f8a

RESEARCH PRODUCT

Synthesis of bodinieric acids A and B, both C-18 and C-19-functionalized abietane diterpenoids: DFT study of the key aldol reaction

Ramón J. ZaragozáMiguel A. González-cardenete

subject

Steric effects010405 organic chemistryStereochemistryGeneral Chemical EngineeringGeneral Chemistry010402 general chemistry01 natural sciences0104 chemical scienceschemistry.chemical_compoundchemistryAldol reactionHydrogen–deuterium exchangeAbietic acidAbietane

description

[EN] The first synthesis of C-18- and C-19-bifunctionalized abietane diterpenoids, bodinieric (or callicapoic) acids, via an aldol reaction has been developed. This key aldol reaction was very sensitive to steric hindrance. This fact has been studied by deuterium exchange experiments and DFT methods. Optimization of this reaction led to the synthesis of anti-inflammatory bodinieric acids A and B, starting from abietic acid

10.13039/501100003339https://dx.doi.org/10.1039/d0ra02711a