Beilstein J. Org. Chem.2021,17, 1440–1446, doi:10.3762/bjoc.17.99
Memory Zimuwandeyi Manuel A. Fernandes Amanda L. Rousseau Moira L. Bode Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag 3, PO WITS, 2050, South Africa 10.3762/bjoc.17.99 Abstract Pavettamine, a plant toxin first isolated from Pavetta harborii in
first total synthesis of the enantiomer of pavettamine, ent-pavettamine. The symmetrical structure of the molecule allows for the synthesis of a common C5 fragment that can be divergently transformed into two synthons for later convergent coupling to furnish the target carbon framework. Based on the
success of the protocol we employed for the synthesis of the naturally occurring pavettamine, (S)-malic acid was again the starting material of choice for the synthesis of the two individual C5 fragments, with strategic differences in terminal-group manipulation allowing for the synthesis of ent
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Graphical Abstract
Figure 1:
Structure of pavettamine 1 and its enantiomer 2.