Concise entry to both enantiomers of 8-oxabicyclo[3.2.1]oct-3-en-2-one based on novel oxidative etherification: formal synthesis of (+)-sundiversifolide |
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| Authors: | Kawasumi Muneo Kanoh Naoki Iwabuchi Yoshiharu |
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| Institution: | Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan. |
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| Abstract: | Both enantiomers of 8-oxabicyclo3.2.1]oct-3-en-2-one (6) have been synthesized from 4-hydroxycyclohept-2-enone (3) on the basis of a novel oxidative cyclo-etherification using PhI(OH)OTs (Koser's reagent). (-)-(1S,5R)-8-Oxabicyclo3.2.1]oct-3-en-2-one (-)-6, 95% ee] was expeditiously transformed to (+)-sundiversifolide (1). |
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