Synthesis of ent-Alantrypinone

Autor:	David J. Hart, Nabi A. Magomedov
Rok vydání:	2001
Předmět:	chemistry.chemical_classification Indole test Stereochemistry Stereoisomerism General Chemistry Oxime Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry chemistry Oxindole Enantiomer Quinazolinone Isomerization Nitrile ylide
Zdroj:	Journal of the American Chemical Society. 123:5892-5899
ISSN:	1520-5126 0002-7863
Popis:	This paper presents a synthesis of ent-alantrypinone (ent-6), the enantiomer of a natural product produced by the fungus Penicillium thymicola. The synthesis revolves around the Li[Me(3)AlSPh]-promoted isomerization of iminobenzoxazine 33 to quinazolinone 34, an N-acyliminium ion cyclization that converts enamide 9 to bridged indole 35, and rearrangement of 35 to oxindole ent-6. Ancillary chemistry that involves thermal fragmentation of an iminobenzoxazine to a nitrile ylide and Me(2)AlSPh-mediated cyclization of oxime ether-ester 22 to pyrrolidinone 23 is also described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::34bc76caea136bf51c79d8f6c98a10ca https://doi.org/10.1021/ja010066+ Zobrazit plný text záznamu