SUBSTITUTED 1,7-DIOXABICYCLO[3.3.0]OCTANES - NEW EASY ACCESS TO THE PERHYDROFUROFURAN CORE OF AFLATOXINS AND ANALOGS

Authors
ALONSO F LORENZO E YUS M
Citation
F. Alonso et al., SUBSTITUTED 1,7-DIOXABICYCLO[3.3.0]OCTANES - NEW EASY ACCESS TO THE PERHYDROFUROFURAN CORE OF AFLATOXINS AND ANALOGS, Tetrahedron letters, 38(12), 1997, pp. 2187-2190
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
12
Year of publication
1997
Pages
2187 - 2190
Database
ISI
SICI code
0040-4039(1997)38:12<2187:S1-NEA>2.0.ZU;2-P
Abstract
The reaction of 3-chloro-2-(chloromethyl)-1-propene(1) with lithium an d a catalytic amount of naphthalene in the presence of different carbo nyl compounds in THF a -78 degrees C affords, after hydrolysis, the co rresponding methylenic diols 2, which by a tandem hydroboration-oxidat ion with hydrogen peroxide followed by treatment with PCC (for ketone derivatives) or RuCl2(PPh(3))(3) (for aldehyde derivatives) yields the expected perhydrofurofurans 3. (C) 1997 Elsevier Science Ltd.