Application of Ferrocenylalkyl Chiral Auxiliaries to Syntheses of Indolenine Alkaloids: Enantioselective Syntheses of Vincadifformine, ψ- and 20-epi-ψ-Vincadifformines, Tabersonine, Ibophyllidine, and Mossambine

Autor:	Martin E. Kuehne, Upul K. Bandarage, Yun-Long Li, Tiansheng Wang, Abdelhakim Hammach
Rok vydání:	1998
Předmět:	Chiral auxiliary biology Chemistry Stereochemistry Organic Chemistry Tabersonine Enantioselective synthesis Diastereomer Strychnos biology.organism_classification Cleavage (embryo) Ring (chemistry) chemistry.chemical_compound Aspidosperma
Zdroj:	The Journal of Organic Chemistry. 63:2172-2183
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo971838g
Popis:	Condensations of the chiral N-ferrocenylethylindoloazepines 4a,b, with the aldehydes 5, 13, 19, 29, and 32, led to tetracyclic vinylogous urethanes 6a,b and 7, 14a and 14b, 21a,c and 21b,d, 30a and 31a, and 30b and 31b. Respectively, 6:1, 5:1, 3:1, 1.7:1, and 2:1 diastereomeric selections provided intermediates which, on cleavage of the chiral auxiliary N-substituent and subsequent elaboration of ring D of the Aspidosperma and Strychnos alkaloids, provided enantiomerically pure (−)-ψ- and (−)-epi-ψ-vincadifformines (1, 2), (+)-ibophyllidine (12), (+)- and (−)-vincadifformine (16a, 16b), (−)-tabersonine (27), and (−)-mossambine (41).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::312ff31f056bd53b162123bc75ae22ef https://doi.org/10.1021/jo971838g Zobrazit plný text záznamu