Citation: Su Yun LIU, Dao Fei HUANG, Hai Hong HUANG, Liang HUANG. Asymmetric Synthesis of (3R, 5R)-3-((tert-Butyldimethylsily)oxy)-5-((Z)-2-Bromovinyl)-Tetrahydro-Furan-2-one, an Intermediate for the Synthesis of Fostriecin[J]. Chinese Chemical Letters, ;2000, 11(11): 957-960. shu

Asymmetric Synthesis of (3R, 5R)-3-((tert-Butyldimethylsily)oxy)-5-((Z)-2-Bromovinyl)-Tetrahydro-Furan-2-one, an Intermediate for the Synthesis of Fostriecin

Institute of Materia Medica, Chinese Academy of Medical Science & Peking Union Medical College, Beijing 100050

Received Date: 8 May 2000

(3R,5R)-3-((tert-Butyldimethylsily)oxy)-5-((Z)-2-bromovinyl)-tetrahydro-furan-2-one, an intermediate for the synthesis of Fostriecin was achieved by intramolecular asymmetric induction in propene addition of (-)-8-phenylmenthyl glyoxylate followed by inversion of C₃-hydroxyl group and Sharpless asymmetric dihydroxylation with simultaneous cyclization to give lactone 5. Then protection of C₃-hydroxyl group and oxidation of the C₆-primary hydroxyl group which reacted with Wittig reagent to yield the target compound4.
- Fostriecin,
- dihydroxylation,
- (-)-8-phenylmenthol asymmetric synthes
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