Ring size effects in the C2–C6 biradical cyclisation of enyne–allenes and the relevance for neocarzinostatin

Autor:	Michael Maywald, Jens-Peter Steffen, Bernd Engels, Patrick W. Musch, Holger Helten, Michael Schmittel
Rok vydání:	2001
Předmět:	Ring size chemistry.chemical_compound Neocarzinostatin Enyne Chemistry Stereochemistry medicine Cyclopentene Moiety Regioselectivity Cycloalkene Ene reaction medicine.drug
Zdroj:	Journal of the Chemical Society, Perkin Transactions 2. :1331-1339
ISSN:	1364-5471 1472-779X
Popis:	The regioselectivity of the thermal cyclisations of enyne–allenes 1 can be toggled as a function of the ring size of the cycloalkene. With a cyclopentene as the ene moiety the Myers–Saito (C2–C7) cycloaromatisation product is formed, whereas with six- and seven-membered cycloalkenes the novel C2–C6 cyclisation is observed. DFT calculations are used to rationalise these changes. The implications of these findings for alternative thermal biradical cyclisations of neocarzinostatin are discussed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ff8c359226e3f5380d823ac820e30497 https://doi.org/10.1039/b102380m Zobrazit plný text záznamu