Synthesis of (+)-Spirolaxine Methyl Ether
- 11 July 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (16) , 6277-6280
- https://doi.org/10.1021/jo060839i
Abstract
A short and efficient synthesis of (+)-spirolaxine methyl ether, a metabolite of the fungus Sporotrichum laxum with inhibitory activity against Helicobacter pylori, is described. The synthesis has been carried out by a Prins cyclization, to obtain the [6,5]-spiroketal system, and a Wadsworth−Emmons condensation, applied for the installation of the polymethylene chain on the phthalide moiety.Keywords
This publication has 12 references indexed in Scilit:
- Utilization of an Oxonia-Cope Rearrangement as a Mechanistic Probe for Prins CyclizationsJournal of the American Chemical Society, 2005
- Synthesis of (−)-Centrolobine by Prins Cyclizations that Avoid RacemizationOrganic Letters, 2002
- The Treatment ofHelicobacter pyloriInfection in the Management of Peptic Ulcer DiseaseNew England Journal of Medicine, 1995
- Helicobacter pylori: Its Role in DiseaseClinical Infectious Diseases, 1992
- Lewis acid-mediated condensation of alkenols and aldehydes. A selective synthesis of tetrahydropyrans and oxepanesThe Journal of Organic Chemistry, 1988
- Facile anhydride synthesis using trichlorotrifluoroacetone hydrateThe Journal of Organic Chemistry, 1986
- Bioactive marine metabolites. Part 16. Calyculin A. A novel antitumor metabolite from the marine sponge Discodermia calyxJournal of the American Chemical Society, 1986
- 1,7-Dioxaspiro[5.5]undecanes. An excellent system for the study of stereoelectronic effects (anomeric and exo-anomeric effects) in acetalsCanadian Journal of Chemistry, 1981
- The chemistry of 2-methyltetrahydropyran-4-one: An L-Selectride reaction that gives predominantly the equatorial alcoholCanadian Journal of Chemistry, 1978
- BIOSYNTHESIS OF LASALOCID. IIThe Journal of Antibiotics, 1974