Synthesis and absolute configuration of the antiparasitic furanosesquiterpenes (-)-furodysin and (-)-furodysinin. Camphor as a six-membered ring chiral pool template
                                
                                    
                                        作者:Valerie Vaillancourt、Mohamad R. Agharahimi、Uma N. Sundram、Olivier Richou、D. John Faulkner、Kim F. Albizati                                    
                                    
                                        DOI:10.1021/jo00001a069
                                    
                                    
                                        日期:1991.1
                                    
                                    The syntheses of (-)-furodysin ((-)-2a) and (-)-furodysinin ((-)-3a) in four steps starting from (+)-9-bromocamphor (18) has been accomplished, thus establishing the absolute configuration of these and related metabolites.  This was made possible by the unexpected exo selectivity in the aldol condensation of camphor-like enolates with aldehydes.  This has been found to be a general phenomenon in the camphor system.  Further, anionic fragmentation of the C1-C7 bond of camphor derivatives has allowed access to synthetic intermediates containing functionalized six-membered rings, thus opening up avenues from camphor to a new class of chiral pool elements not currently available from chiral pool substances.