Synthesis of arylspiroketals related to the papulacandins via generation of phthalide oxycarbenium ions

Authors
Brimble, MA Caprio, V Johnston, AD Sidford, M
Citation
Ma. Brimble et al., Synthesis of arylspiroketals related to the papulacandins via generation of phthalide oxycarbenium ions, SYNTHESIS-S, (6), 2001, pp. 855-862
Citations number
39
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
6
Year of publication
2001
Pages
855 - 862
Database
ISI
SICI code
0039-7881(200105):6<855:SOARTT>2.0.ZU;2-R
Abstract
The nucleophilic addition of allylstannanes to oxycarbenium ions generated from phthalide acetate has been studied. The optimum conditions involve the use of trimethylsilyl trifluoromethanesulfonate in dichloromethane at -78 degreesC. Hydroboration of the allylated products followed by oxidative cyc lization provides an efficient synthesis of arylspiroketals which are close ly related to the papulacandins.