Effects of propargylic substitution and annelation on the cycloaromatization of a bicyclo[7.3.1] enediyne

Authors
Moss, DK Spence, JD Nantz, MH
Citation
Dk. Moss et al., Effects of propargylic substitution and annelation on the cycloaromatization of a bicyclo[7.3.1] enediyne, J ORG CHEM, 64(12), 1999, pp. 4339-4343
Citations number
36
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
12
Year of publication
1999
Pages
4339 - 4343
Database
ISI
SICI code
0022-3263(19990611)64:12<4339:EOPSAA>2.0.ZU;2-A
Abstract
The cycloaromatization kinetics of two bicyclo[7.3.1] enediynes are present ed. Silyl protection of a propargylic alcohol positioned on the enediyne co re was found to moderate enediyne cycloaromatization. However, the presence of multiple fused ring systems exerts geometrical constraints that prevent cycloaromatization of the otherwise facile cyclization previously observed for the core system.