USE OF DIAZOPHOSPHONATES IN THE SYNTHESIS OF CYCLIC ETHERS .2. SYNTHESIS OF THE PYRANOOXEPANE AND OXEPANOOXEPANE SUBUNITS OF MARINE POLYETHER TOXINS

Authors
MOODY CJ SIE ERHB KULAGOWSKI JJ
Citation
Cj. Moody et al., USE OF DIAZOPHOSPHONATES IN THE SYNTHESIS OF CYCLIC ETHERS .2. SYNTHESIS OF THE PYRANOOXEPANE AND OXEPANOOXEPANE SUBUNITS OF MARINE POLYETHER TOXINS, Journal of the Chemical Society. Perkin transactions. I, (5), 1994, pp. 501-506
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
5
Year of publication
1994
Pages
501 - 506
Database
ISI
SICI code
0300-922X(1994):5<501:UODITS>2.0.ZU;2-G
Abstract
3-Oxooxepan-2-ylphosphonates 3, prepared by rhodium carbenoid cyclisat ion of the diazophosphonates 1, are readily elaborated into the keto a lcohols 6, by Wadsworth-Emmons reaction, hydrogenation and epimerisati on. Cyclisation of 6 using trimethylsilyl triflate-triethylsilane resu lts in formation of 7-6- and 7-7-bicyclic ethers 10, with trans select ivity.