Flow Thermolysis Rearrangements in the Indole Alkaloid Series: Strictamine and Akuammicine Derivatives. The Absolute Configurations of Ngouniensine and epi-Ngouniensine

Autor:	Jean Lévy, Marie-José Jacquier, Louisette Le Men-Olivier, G. Hugel, B. Richard, Daniel Royer
Rok vydání:	1997
Předmět:	Indole test chemistry.chemical_compound chemistry Indole alkaloid Akuammicine Stereochemistry Alkaloid Organic Chemistry Thermal decomposition Absolute configuration
Zdroj:	The Journal of Organic Chemistry. 62:578-583
ISSN:	1520-6904 0022-3263
Popis:	Flow thermolysis of strictamine (1) generated two of the predictable rearrangement products, resulting from [1,5]-sigmatropic shifts: akuammicine (2) and indolenine 9. Besides formation of these two compounds, a quite different pathway gave rise to a novel rearrangement leading to indole 6, with the framework of the natural alkaloid ngouniensine (19). Rearrangement to the ngouniensine skeleton became the major pathway when the akuammicine derivatives 10, 12, and 17 were submitted to thermolysis, generating compounds 11, 13 + 15, and 18, respectively. These results allowed us to assign the absolute configuration of (−)-ngouniensine (19) (3R,20R) and that of (−)-epingouniensine ((−)-21) (3R,20S).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::736c0c9ac1bf038e9b499363af49f80a https://doi.org/10.1021/jo961816e Zobrazit plný text záznamu