Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2004(3): 485-488
DOI: 10.1055/s-2004-817746
DOI: 10.1055/s-2004-817746
LETTER
© Georg Thieme Verlag Stuttgart · New York
A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxo-carboxylates
Further Information
Received
17 December 2003
Publication Date:
06 February 2004 (online)
Publication History
Publication Date:
06 February 2004 (online)

Abstract
Enzymatic hydrolysis was applied to the preparation of certain chiral 5-hydroxy-3-oxo-carboxylates that are potential precursors for natural product synthesis via the formation of lactone derivatives and tetrahydropyran rings.
Key words
5-hydroxy-3-oxo-carboxylates - 6-substituted-4-hydroxy lactones - tetrahydropyran-4-ones - Candia Rugosa lipase (CRL) - enzymatic hydrolysis
-
1a
Morrison JD. Asymmetric Synthesis Vol 3B: Academic Press; New York: 1984. -
1b
Bosnich B. Asymmetric Catalysis Vol 5: Martinus Nijihoff; Dordrecht: 1986. p.115 -
1c
Tomioka K. Synthesis 1990, 541 -
1d
Noyori R.Kitamura M. Angew. Chem., Int. Ed. Engl. 1991, 30: 49 -
2a
Endo A.Kuroda M.Tsujita Y. J. Antibiot. 1976, 29: 1346 -
2b
Brown AG.Smale TC.King TJ.Hasenkamp R.Thompson RH. J. Chem. Soc., Perkin Trans. 1 1976, 1165 -
3a
Soriente A.De-Rosa M.Apicella A.Scettri A.Sodano G. Tetrahedron: Asymmetry 1999, 10: 4481 -
3b
Lattman E.Coombs J.Hoffmann HMR. Synthesis 1996, 171 - 4
Hagiwarra H.Kon-no M.Uda H. J. Chem. Soc., Chem. Commun. 1992, 866 - 5
Hagiwarra H.Kimura K.Uda H. J. Chem. Soc., Perkin Trans. 1 1992, 693 - 6
Evans DA.Carber PH.Carreira EM.Prunet JA.Charefte AB.Lautens M. Angew. Chem. Int. Ed. 1998, 37: 2354 - 7
Clarke PA.Martin WHC. Org. Lett. 2002, 4: 4527 -
8a
Rosen T.Heathcock CH. Tetrahedron 1986, 14: 4909 -
8b
Lynch JE.Volante RP.Wattley RV.Shinkai I. Tetrahedron Lett. 1987, 28: 1385 -
8c
Roth BD.Roark WH. Tetrahedron Lett. 1988, 29: 1255 -
8d
Johnson WS.Kelson AB.Elliot JD. Tetrahedron 1988, 29: 3757 -
8e
Boquel P.Chapleur Y. Tetrahedron Lett. 1990, 31: 1869 -
8f
Takano S.Shimazaki Y.Sekiguichi Y.Ogasawara K. Synthesis 1989, 539 -
8g
Shao L.Seki T.Kawano H.Saburi M. Tetrahedron Lett. 1991, 32: 7699 -
8h
Shao L.Kawano H.Saburi M.Uchida Y. Tetrahedron 1993, 49: 1997 -
8i
Bonini C.Pucci P.Viggianni L. J. Org. Chem. 1991, 56: 4050 -
8j
Hayashi M.Inoue T.Oguni N. J. Chem. Soc., Chem. Commun. 1994, 341 -
8k
Oguni N.Tanaka K.Ishida H. Synlett 1998, 601 -
8l
Soriente A.Rosa MD.Stanzione M.Villano R.Scettri A. Tetrahedron: Asymmetry 2001, 12: 959 -
8m
Soriente A.Rosa MD.Villano R.Scettri A. Tetrahedron: Asymmetry 2000, 11: 2255 -
9a
Wong CH.Whitesides GM. Enzymes in Synthetic Organic Chemistry Tetrahedron Organic Series, Pergamon; London: 1994. Chap. 2. p.41 -
9b
Drauz K.Waldmann H. Enzyme Catalysis in Organic Synthesis Vol. II: Weinhein; VCH: 2002. Chap. 11. p.335 -
9c
Faber K. Biotransformations in Organic Chemistry 3rd ed.: Springer-Verlag; Beijing: 1997. Chap. 2. p.23 -
9d
Henkel B.Kunath A.Schick H. Liebigs Ann. Chem. 1992, 809 -
9e
Henkel B.Kunath A.Schick H. Tetrahedron: Asymmetry 1993, 4: 153 -
9f
Henkel B.Kunath A.Schick H. Tetrahedron: Asymmetry 1994, 5: 17 -
10a
Zhang YH.Xu CF.Li JF.Yuan CY. Tetrahedron: Asymmetry 2003, 14: 63 -
10b
Zhang YH.Yuan CY.Li ZY. Tetrahedron 2002, 58: 2973 -
10c
Zhang YH.Li ZY.Yuan CY. Tetradedron Lett. 2002, 43: 3247 - 12
Chen CS.Fujimoto Y.Girdaukas G.Shi CJ. J. Am. Chem. Soc. 1982, 104: 7294 -
13a
Peterson JR.Winter TJ.Miller CP. Synth. Commun. 1988, 18: 949 -
13b
Svendsen A.Boll PM. J. Org. Chem. 1975, 40: 1927 -
13c
Izawa T.Mukaiyama T. Chem. Lett. 1975, 40: 161
References
Conditions of chiral HPLC were recorded in Table [2] .