SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANONES AND TETRAHYDROPYRANONES - PHOTOCYCLOADDITION FRAGMENTATION REACTIONS OF DIOXINONES/

Authors
DRITZ JH CARREIRA EM
Citation
Jh. Dritz et Em. Carreira, SYNTHESIS OF SUBSTITUTED TETRAHYDROFURANONES AND TETRAHYDROPYRANONES - PHOTOCYCLOADDITION FRAGMENTATION REACTIONS OF DIOXINONES/, Tetrahedron letters, 38(32), 1997, pp. 5579-5582
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
32
Year of publication
1997
Pages
5579 - 5582
Database
ISI
SICI code
0040-4039(1997)38:32<5579:SOSTAT>2.0.ZU;2-R
Abstract
The combination of dioxinone aldol addition methodology and [2+2]-phot ocycloaddition/fragmentation reactions can provide access to substitut ed tetrahydrofuran-3-ones and tetrahydropyran-4-ones, subunits abundan tly found in biologically active natural products. Intramolecular phot ocyclization of vinyl and allyl ethers with dioxinones, followed by fr agmentation in alkaline MeOH (K2CO3) leads to tetrahydrofuran-3-ones a nd tetrahydropyran-4-ones, providing a practical route to versatile bu ilding blocks for complex molecule synthesis. (C) 1997 Elsevier Scienc e Ltd.