Reprogramming of the biosynthetic network of Daphniphyllum alkaloids into a chemically synthetic network through generalized biomimetic strategies

11 July 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Biomimetic synthesis is a fundamental approach to the chemical synthesis of natural products, which, due to the intrinsic correlation between the biogenesis and the structure of natural products, offers many advantages. Conventional biomimetic strategies have evolved on a principle featuring “(essentially) the same substrates, similar reactions, and similar pathways”, which defines the pattern of biomimetic synthesis from the structural, mechanistic, and sequential perspectives. In practice, such highly imitative approaches have proved considerably feasible and efficient. However, applicability of this type of approach is also limited by the principle. To enhance the power of biomimetic synthesis, we envision generalized biomimetic strategies focusing on the key bond formation/cleavage sites implied by the biogenesis of natural products, which allow us to take full advantage of altered substrates, reactions, and pathways while retaining the inherent advantages of biomimetic synthesis. In this study, we showcased the utility of generalized biomimetic strategies in the synthesis of fourteen Daphniphyllum alkaloids from the macrodaphniphyllamine, calyciphylline A, daphnilongeranin A, and daphnicyclidin D subfamilies. The biosynthetic network of these alkaloids was reprogrammed into a powerful chemically synthetic network through substrate-, reaction-, and pathway-altering biomimetic strategies.

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