Determination of the Absolute Configuration of Ballonigrin Lactone A Using Density Functional Theory Calculations.

ABSTRACT: We report the determination of the absolute configuration of a diterpenoid, namely, ballonigrin lactone A (BLA), by comparison of the computed optical rotations, [α]_D, of its two diastereomers using density functional theory (DFT) calculations to the experimental [α]_D value of +22.4. One of the diastereomers having configurations 4S, 5R, 6S, 10S, 15S was named "α-BLA," and the other one with configuration 4S, 5R, 6S, 10S, 15R was called "β-BLA". Six conformers for each diastereomer (α-BLA and β-BLA) of BLA were identified through their conformational analysis. [α]_D values of these six conformations for each diastereomer were calculated using DFT at the mPW1PW91/6-311G(d,p)/SMD_Chloroform level of theory, leading to the conformationally averaged [α

SUBMITTER: Naseem M 

PROVIDER: S-EPMC9850775 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature