CONFORMATIONALLY CONTROLLED TRANSANNULAR REACTIONS OF A 12-MEMBERED MACROCYCLIC TRIENOL

Authors
PADRON JI VAZQUEZ JT MORALES EQ ZARRAGA M MARTIN JD
Citation
Ji. Padron et al., CONFORMATIONALLY CONTROLLED TRANSANNULAR REACTIONS OF A 12-MEMBERED MACROCYCLIC TRIENOL, Tetrahedron : asymmetry, 3(3), 1992, pp. 415-430
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
3
Issue
3
Year of publication
1992
Pages
415 - 430
Database
ISI
SICI code
0957-4166(1992)3:3<415:CCTROA>2.0.ZU;2-U
Abstract
Iodine-induced transannular ring enlargements of several epoxide deriv atives of the cyclotrienol (Z,E,Z)-1-hydroxy-cyclododeca-2,5,9-triene (1) are presented. The diastereoselection exhibited by both the inter- and intramolecular reactions studied, appears to be associated with t he conformational preferences of the macrocycle since simple molecular mechanics calculations allowed semiquantitative predictions in the pr oduct distributions. An absolute configurational study based on CD exc iton chirality methodology is also included.