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Volumn 3, Issue 17, 2001, Pages 2777-2779

An enantioselective synthesis of cryptocarya diacetate

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE;

EID: 0035940146     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016399t     Document Type: Article
Times cited : (67)

References (34)
  • 3
    • 0041794668 scopus 로고    scopus 로고
    • note
    • To the best of our knowledge, lactones 1 and 2 have not been named; thus for simplicity reasons we will refer to 1 as cryptocarya diacetate and 2 as cryptocarya triacetate.
  • 8
    • 0042796827 scopus 로고    scopus 로고
    • note
    • The Aldrich Chemical Co. provides (S)-tert-butyl 3-hydroxybutyrate at the cost of $41/mL.
  • 11
    • 0034639734 scopus 로고    scopus 로고
    • For some recent approaches to related 6-substituted 5,6-dihydropyran-2-one containing natural products, see: (a) Gosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003-1006.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 1003-1006
    • Gosh, A.K.1    Bilcer, G.2
  • 20
    • 0034722988 scopus 로고    scopus 로고
    • Leighton has demonstrated that this can be accomplished by the addition of allyl-(-)-diisopinocamphenylborane to similarly protected aldehydes, but we hoped to find a less expensive alternative. Hornberger, K. R.; Hamblett, C. L.; Leighton, J. L. J. Am. Chem. Soc. 2000, 122, 12894.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12894
    • Hornberger, K.R.1    Hamblett, C.L.2    Leighton, J.L.3
  • 21
    • 0028071712 scopus 로고
    • The syn-1,3-diol structural unit is a common motif in many natural products, with a wide range of biological activities. (a) Rychnovsky, S. D.; Hoye, R. C. J. Am. Chem. Soc. 1994, 116, 1753-1765.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1753-1765
    • Rychnovsky, S.D.1    Hoye, R.C.2
  • 24
    • 0041294096 scopus 로고    scopus 로고
    • note
    • The Aldrich Chemical Co. sells ethyl sorbate for $0.30/g.
  • 25
    • 33947086629 scopus 로고
    • All levels of enantioinduction were determined by HPLC analysis (8% IPA/hexane, Chiralcel OD) and/or Mosher ester analysis. (a) Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143.
    • (1973) J. Org. Chem. , vol.38 , pp. 2143
    • Sullivan, G.R.1    Dale, J.A.2    Mosher, H.S.3
  • 27
    • 0041294097 scopus 로고    scopus 로고
    • note
    • 13C NMR, FTIR, and HRMS.
  • 30
    • 0042295801 scopus 로고    scopus 로고
    • note
    • This lower than normal (2:1 phosphine to palladium) ratio gave higher yields and faster reaction times.
  • 32
    • 0041294098 scopus 로고    scopus 로고
    • note
    • Others have noted low yields for similar acylations with acryloyl chloride, see ref 10e.
  • 33
    • 0032580376 scopus 로고    scopus 로고
    • For a excellent review on ring closing metathesis reactions, see: Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 34
    • 0035850265 scopus 로고    scopus 로고
    • For other uses of ring closing metathesis reactions for the formation of pyranones, see: ref 10a,b,e and Cossy, J.; Pradaux, F.; Bouzbouz, S. Org. Lett. 2001, 3, 2233-2235.
    • (2001) Org. Lett. , vol.3 , pp. 2233-2235
    • Cossy, J.1    Pradaux, F.2    Bouzbouz, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.