STUDIES IN MARINE MACROLIDE SYNTHESIS - BORON AND SILICON-MEDIATED COUPLING STRATEGIES FOR SWINHOLIDE-A

Authors
PATERSON I CUMMING JG SMITH JD WARD RA
Citation
I. Paterson et al., STUDIES IN MARINE MACROLIDE SYNTHESIS - BORON AND SILICON-MEDIATED COUPLING STRATEGIES FOR SWINHOLIDE-A, Tetrahedron letters, 35(3), 1994, pp. 441-444
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
3
Year of publication
1994
Pages
441 - 444
Database
ISI
SICI code
0040-4039(1994)35:3<441:SIMMS->2.0.ZU;2-C
Abstract
Reaction of aldehyde 6 with enol borinates 7 gives adduct 10 preferent ially, whereas the allylsilane 18 provides the epimeric adduct 11 with 95% ds. Aldehyde 2 reacts mainly by si-face attack with simple Z enol borinates, which can be overturned by reagent control from (+)-25.