1198616-20-4Relevant academic research and scientific papers
Total synthesis of ent-pavettamine
Bode, Moira L.,Fernandes, Manuel A.,Rousseau, Amanda L.,Zimuwandeyi, Memory
, p. 1440 - 1446 (2021/06/16)
Pavettamine, a plant toxin first isolated from Pavetta harborii in 1995, was previously identified as a polyamine with C2 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 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-pavettamine rather than pavettamine. Chain extension and stereoselective ketone reduction were achieved using the (R)-methyl p-tolyl sulfoxide chiral auxiliary to give the desired 1,3-syn-diol C5 unit. A protecting-group strategy was also developed for the orthogonal protection of the alcohol and amine functional groups as they were unveiled. The functionalized C5 fragments were coupled via reductive amination revealing the C10 carbon backbone. Deprotection of the alcohol and amine functional groups successfully provided ent-pavettamine as a TFA salt.
Structure elucidation and stereoselective total synthesis of pavettamine, the causal agent of gousiekte
Bode, Moira L.,Gates, Paul J.,Gebretnsae, Samson Y.,Vleggaar, Robert
experimental part, p. 2026 - 2036 (2010/04/26)
The structure elucidation of a novel natural product pavettamine (1), the causal agent of the plant toxicosis gousiekte, is reported. The structure was defined by analysis of NMR and MS data and the relative configuration followed from the 13C NMR data of the acetonide derivative. The absolute stereochemistry was established by total synthesis from (2S)-malic acid using chiral sulfoxide methodology as (2S,4R,8R,10S)-1,11-diamino-6-aza-undecane-2,4,8,10-tetraol.
NEW COMPOUNDS FOR THE TREATMENT OF CANCER
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Page/Page column 14; 26, (2009/12/28)
The invention provides a method of preparing the stereoisomers of 1,11-diamino-6-aza- undecane-2,4,8,10-tetraol.
