Second-generation, highly abbreviated route for elaboration of the oxetane D-ring in a fully functionalized taxane.
A six-step conversion of oxirane 3 to oxetane 9 is reported. The synthetic route takes particular advantage of the acid-catalyzed ring opening of 3 to allyl alcohol 4 in a polar reaction medium and of the heightened capability of the OsO4.TMEDA complex to effect the efficient stereocontrolled dihydroxylation of this intermediate. The overall yield of the new sequence is 33%.
Brennan
Nancy K
NK
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
Guo
Xin
X
Paquette
Leo A
LA
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry*; D005027:Ethylene Oxide / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D043823:Taxoids / Q000138:chemical synthesis* / Q000737:chemistry
D001952:Bridged-Ring Compounds; D004988:Ethers, Cyclic; D043823:Taxoids; C080625:taxane; C005287:oxetane; D005027:Ethylene Oxide