Synthesis of functionalized gamma-spirolactone and 2-oxabicyclo[3.3.0]octane derivatives from nucleophilic oxirane ring opening

Authors
Santos, MRD Barreiro, EJ Braz, R Fraga, CAM
Citation
Mrd. Santos et al., Synthesis of functionalized gamma-spirolactone and 2-oxabicyclo[3.3.0]octane derivatives from nucleophilic oxirane ring opening, TETRAHEDRON, 56(30), 2000, pp. 5289-5295
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
30
Year of publication
2000
Pages
5289 - 5295
Database
ISI
SICI code
0040-4020(20000721)56:30<5289:SOFGA2>2.0.ZU;2-J
Abstract
Methyl 1-(2-oxiranylmethyl)-2-oxo-1-cyclopentanecarboxylate (4) was subject ed to the nucleophilic ring opening reaction, leading to the formation of t he functionalized 2-oxaspiro[4.4]nonane and 2-oxabicyclo[3.3.0]octane deriv atives. which are important structural sub-unit present in several classes of bioactive compounds. The products obtained were characterized on the bas is of spectral data, including 1D and 2D NMR. (C) 2000 Elsevier Science Ltd . All rights reserved.