Dimerization of o-hydroxycyclohexadienones related to calicheamicinone: S(N)2 displacement of the 12 alpha-hydroxyl group

Authors
Churcher, I Hallett, D Magnus, P
Citation
I. Churcher et al., Dimerization of o-hydroxycyclohexadienones related to calicheamicinone: S(N)2 displacement of the 12 alpha-hydroxyl group, TETRAHEDRON, 55(6), 1999, pp. 1597-1606
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
6
Year of publication
1999
Pages
1597 - 1606
Database
ISI
SICI code
0040-4020(19990205)55:6<1597:DOORTC>2.0.ZU;2-P
Abstract
Deprotection of the readily available bicyclo[7.3.1]enediyne alcohol 14 res ulted in dimerization to give 18. Replacement of the 12 alpha-hydroxyl grou p with a p-methoxyanilino group proceeded with overall retention to give 23 which also produced a dimer on attempted deprotection. (C) 1999 Elsevier S cience Ltd. All rights reserved.