Abstract
Although computational simulation-based natural product syntheses are in their initial stages of development, this concept can potentially become an indispensable resource in the field of organic synthesis. Herein we report the asymmetric total syntheses of several resveratrol dimers based on a comprehensive computational simulation of their biosynthetic pathways. Density functional theory (DFT) calculations suggested inconsistencies in the biosynthesis of vaticahainol A and B that predicted the requirement of structural corrections of these natural products. According to the computational predictions, total syntheses were examined and the correct structures of vaticahainol A and B were confirmed. The established synthetic route was applied to the asymmetric total synthesis of (−)-malibatol A, (−)-vaticahainol B, (+)-vaticahainol A, (+)-vaticahainol C, and (−)-albiraminol B, which provided new insight into the biosynthetic pathway of resveratrol dimers. This study demonstrated that computation-guided organic synthesis can be a powerful strategy to advance the chemical research of natural products.
Highlights
Computational simulation-based natural product syntheses are in their initial stages of development, this concept can potentially become an indispensable resource in the field of organic synthesis
We performed Density functional theory (DFT) calculations to simulate the biosynthetic pathway of resveratrol dimers, which suggested that the structures of vaticahainol A and B required corrections
Total synthesis according to the predicted biosynthetic pathway confirmed the correct structures of vaticahainol A and B
Summary
Computational simulation-based natural product syntheses are in their initial stages of development, this concept can potentially become an indispensable resource in the field of organic synthesis. Computational programs that can simulate ideas for complex molecule synthesis and verify the validity of synthetic plans provide a precise guide for conducting efficient experiments in real laboratory settings Such techniques are in their initial stages of development, they will potentially become indispensable resources in the field of organic synthesis[1,2,3]. The pharmacological profiles and structural complexity of ROs have made them attractive targets for synthetic organic chemists[11,12,13,14,15,16,17] Owing to their structural complexity deriving from the diverse oligomerization patterns and large number of stereocenters, as well as the low amounts isolable from plant resources, considerable effort is required to determine the structures by natural product chemistry research techniques. We report the computation-guided total synthesis and structural correction of vaticahainol A and B based on comprehensive DFT calculations of the biosynthetic pathways. Asymmetric total syntheses of the (+)- and (−)-enantiomers of malibatol A and vaticahainol A, B, and C (albiraminol B) are achieved by late-stage kinetic resolution using an enantioselective acylation of a racemic malibatol A derivative
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