A NOVEL ROUTE TO MONOANOMERIC SPIROKETALS

Authors
ZEMRIBO R MEAD KT
Citation
R. Zemribo et Kt. Mead, A NOVEL ROUTE TO MONOANOMERIC SPIROKETALS, Tetrahedron letters, 39(23), 1998, pp. 3891-3894
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
23
Year of publication
1998
Pages
3891 - 3894
Database
ISI
SICI code
0040-4039(1998)39:23<3891:ANRTMS>2.0.ZU;2-2
Abstract
A series of spiroketal C2-acetals was treated with an alkylsilane reag ent in the presence of either TMSOTf or BF3.OEt2 to effect C2-substitu tion. Regioselective alkylation was successful, but in each case a mon oanomeric spiroketal was the unexpected major product. The sequence pr ovides a model for the synthesis of the CD subunit of altohyrtin A. (C ) 1998 Elsevier Science Ltd. All rights reserved.