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Microgrewiapine C: Asymmetric Synthesis, Spectroscopic Data, and Configuration Assignment.

ABSTRACT: The first asymmetric synthesis of microgrewiapine C, a piperidine alkaloid isolated from Microcos paniculata, is reported. This synthesis prompted correction of the ¹H and ¹³C NMR data for the natural sample of the alkaloid, which was achieved by reanalysis of the original spectra. The corrected data for the natural product were found to be identical to those of the synthetic sample prepared herein, thus confirming the structural and relative configurational assignment of microgrewiapine C. Although comparison of specific rotation values indicates that the (1R,2S,3S,6S) absolute configuration should be assigned to the alkaloid, consideration of potential common biosynthetic origins of microgrewiapine C and congeners suggests that further phytochemical investigations are warranted.

SUBMITTER: Davies SG

PROVIDER: S-EPMC9315977 | biostudies-literature | 2022 Jul

REPOSITORIES: biostudies-literature

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Microgrewiapine C: Asymmetric Synthesis, Spectroscopic Data, and Configuration Assignment.

Davies Stephen G SG Fletcher Ai M AM Roberts Paul M PM Taylor Cameron E CE Thomson James E JE

Journal of natural products 20220630 7

The first asymmetric synthesis of microgrewiapine C, a piperidine alkaloid isolated from Microcos paniculata, is reported. This synthesis prompted correction of the 1H and 13C NMR data for the natural sample of the alkaloid, which was achieved by reanalysis of the original spectra. The corrected data for the natural product were found to be identical to those of the synthetic sample prepared herein, thus confirming the structural and relative configurational assignme ...[more]

PMID: 35771599

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