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Volumn 133, Issue 43, 2011, Pages 17494-17503

Divergent synthesis and chemical reactivity of bicyclic lactone fragments of complex rearranged spongian diterpenes

Author keywords

[No Author keywords available]

Indexed keywords

ACETOXYLATION; BASIC CONDITIONS; BIOLOGICAL PROPERTIES; CARBONYL GROUPS; CYCLIZATION REACTIONS; DITERPENES; DIVERGENT SYNTHESIS; GOLGI MEMBRANE; LYSINE SIDE CHAINS; ONE-RING SYSTEMS; PRIMARY AMINES; QUATERNARY CARBON;

EID: 80054987085     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja207727h     Document Type: Article
Times cited : (25)

References (59)
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    • For an example of a similar functionalization, see ref 7b.
    • For an example of a similar functionalization, see ref 7b.
  • 32
    • 80054974098 scopus 로고    scopus 로고
    • IBX in DMSO/toluene generated regioisomeric enone products as a 1:1 mixture. Similarly, reaction conditions such as PhSCl in MeCN or LDA, PhSSPh in THF provided unselective introduction of the sulfur unit.
    • IBX in DMSO/toluene generated regioisomeric enone products as a 1:1 mixture. Similarly, reaction conditions such as PhSCl in MeCN or LDA, PhSSPh in THF provided unselective introduction of the sulfur unit.
  • 43
    • 0037241494 scopus 로고    scopus 로고
    • Steric shielding must be involved, as 1-(trimethylsiloxy)cyclopentene is a much stronger nucleophile than ethyl vinyl ether; see
    • Steric shielding must be involved, as 1-(trimethylsiloxy)cyclopentene is a much stronger nucleophile than ethyl vinyl ether; see: Mayr, H.; Kempf, H.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66
    • (2003) Acc. Chem. Res. , vol.36 , pp. 66
    • Mayr, H.1    Kempf, H.2    Ofial, A.R.3
  • 47
    • 79960928606 scopus 로고    scopus 로고
    • The use of dry DMF was critical for efficient cyclization. For a discussion of the role of DMF in glycosylation chemistry, see
    • The use of dry DMF was critical for efficient cyclization. For a discussion of the role of DMF in glycosylation chemistry, see: Lu, S.; Lai, Y.; Chen, J.; Liu, C.; Mong, K. T. Angew. Chem., Int. Ed. 2011, 50, 7315
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 7315
    • Lu, S.1    Lai, Y.2    Chen, J.3    Liu, C.4    Mong, K.T.5
  • 56
    • 0000237619 scopus 로고
    • For a discussion of the differences in reactivity between five- and six-membered lactones, see
    • For a discussion of the differences in reactivity between five- and six-membered lactones, see: Brown, H. C.; Brewster, J. H.; Shechter, H. J. Am. Chem. Soc. 1954, 76, 467
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 467
    • Brown, H.C.1    Brewster, J.H.2    Shechter, H.3
  • 58
    • 80055009462 scopus 로고    scopus 로고
    • The Modification of Amino Groups
    • In, 3 rd ed. CRC Press: Washington, DC
    • The Modification of Amino Groups. In Chemical Reagents for Protein Modification, 3 rd ed.; Lundblad, R. L., Ed.; CRC Press: Washington, DC, 2005; pp 31-67.
    • (2005) Chemical Reagents for Protein Modification , pp. 31-67
    • Lundblad, R.L.1
  • 59
    • 0026625689 scopus 로고
    • A similar lysine modification pattern is observed in the acylation of HEWL by acetic anhydride; see
    • A similar lysine modification pattern is observed in the acylation of HEWL by acetic anhydride; see: Suckau, D.; Mak, M.; Przybylski, M. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5630
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 5630
    • Suckau, D.1    Mak, M.2    Przybylski, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.