Total synthesis of ent-pavettamine.

ABSTRACT: Pavettamine, a plant toxin first isolated from Pavetta harborii in 1995, was previously identified as a polyamine with C ₂ symmetry and a 1,3-syn-diol moiety on a C₁₀ carbon backbone - one of very few substituted polyamines to be isolated from nature. Its absolute configuration was later established by our first reported total synthesis in 2010. Herein we report the 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 naturall

SUBMITTER: Zimuwandeyi M 

PROVIDER: S-EPMC8204129 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature