A Preferred Intramolecular ‘Ene’ Reaction Between Ketene and Olefin

Autor:	S. M. Kher, G. H. Kulkarni, R. B. Mitra
Rok vydání:	1989
Předmět:	chemistry.chemical_compound Olefin fiber Chemistry Stereochemistry Intramolecular force Organic Chemistry Ketene Organic chemistry Cyclobutanone Sesquiterpene Cyclopentanone Ene reaction Aplysia kurodai
Zdroj:	Synthetic Communications. 19:597-604
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397918908050704
Popis:	Aplysin (1), a marine sesquiterpene was isolated from ‘aplysia kurodai’ and its structure was ellucidated by Hirata-et-al1. They also reported the synthesis of racemic aplysin2. Their synthetic route involved cyclopentanone (2) as a well-characterized intermediate. We visualized the synthesis of cyclobutanone (3) and its subsequent conversion to (2) as an attractive alternative. But during our attempts to synthesize the said cyclobutanone, we have come across a very facile intramolecular ‘ene’ reaction between ketene and olefin. We report our unexpected observations in this communication.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2869e15542a5945cc4cf88f0d057000d https://doi.org/10.1080/00397918908050704 Zobrazit plný text záznamu