ACTIVATION OF A DIENEDIYNE MODEL OF NEOCARZINOSTATIN CHROMOPHORE THROUGH AN ACID-MEDIATED SOLVOLYSIS - EVIDENCE FOR A NEW CYCLIZATION MODE OF ENYNE[3]CUMULENES

Authors
SCHEUPLEIN SW MACHINEK R SUFFERT J BRUCKNER R
Citation
Sw. Scheuplein et al., ACTIVATION OF A DIENEDIYNE MODEL OF NEOCARZINOSTATIN CHROMOPHORE THROUGH AN ACID-MEDIATED SOLVOLYSIS - EVIDENCE FOR A NEW CYCLIZATION MODE OF ENYNE[3]CUMULENES, Tetrahedron letters, 34(41), 1993, pp. 6549-6552
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
41
Year of publication
1993
Pages
6549 - 6552
Database
ISI
SICI code
0040-4039(1993)34:41<6549:AOADMO>2.0.ZU;2-R
Abstract
When treated with 0.1 equiv. of triflic acid, a solution of the Z-conf igurated dienediyne 19 in a 2:3 mixture of tert-BuSH and CH2Cl2 furnis hed the brightly yellow enyne[3]cumulene 20 through a S(N)''-reaction. 20 reacted at room temperature through a Saito-Myers cyclization to t he substituted styrenes 31 and 24 and through an unprecedented cyclois omerization to the anthracene 25.