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Volumn 70, Issue 23, 2005, Pages 9447-9462

Synthesis of all 16 stereoisomers of pinesaw fly sex pheromones - Tools and tactics for solving problems in fluorous mixture synthesis

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ISOMERS; SYNTHESIS (CHEMICAL);

EID: 27744539009     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051526a     Document Type: Article
Times cited : (43)

References (35)
  • 7
    • 0034840718 scopus 로고    scopus 로고
    • For reviews of chromatography with fluorous silica gel, see: (a) Curran, D. P. Synlett 2001, 1488-1496.
    • (2001) Synlett , pp. 1488-1496
    • Curran, D.P.1
  • 8
    • 4344670215 scopus 로고    scopus 로고
    • Gladysz, J. A., Horvath, I. T., Curran, D. P., Eds.; Wiley-VCH: Weinheim
    • (b) Curran, D. P. In The Handbook of Fluorous Chemistry; Gladysz, J. A., Horvath, I. T., Curran, D. P., Eds.; Wiley-VCH: Weinheim, 2004; pp 128-156.
    • (2004) The Handbook of Fluorous Chemistry , pp. 128-156
    • Curran, D.P.1
  • 9
    • 0037835827 scopus 로고    scopus 로고
    • (c) Zhang, W. Tetrahedron 2003, 59, 4475-4489.
    • (2003) Tetrahedron , vol.59 , pp. 4475-4489
    • Zhang, W.1
  • 13
  • 16
    • 27744573028 scopus 로고    scopus 로고
    • note
    • The phermone structures are consistently drawn such that a stereocenter with an "up" group is R and a stereocenter with a "down" group is S. Configurations are always listed in the order C2, C3, C7, C11.
  • 18
    • 0345868588 scopus 로고    scopus 로고
    • (a) Fluorous mixture synthesis has recently been used to make a 16-member stereoisomer library of murisolins for rigorous structure assignment. See: Zhang, Q.; Lu, H.; Richard, C.; Curran, D. P. J. Am. Chem. Soc. 2004, 126, 36-37.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 36-37
    • Zhang, Q.1    Lu, H.2    Richard, C.3    Curran, D.P.4
  • 19
    • 24344493479 scopus 로고    scopus 로고
    • (b) For a recent Concept Article and quasi-enantiomers and other quasi-isomers, see: Zhang, Q.; Curran, D. P. Chem.-Eur. J. 2005, 11, 4866-4880.
    • (2005) Chem.-Eur. J. , vol.11 , pp. 4866-4880
    • Zhang, Q.1    Curran, D.P.2
  • 21
    • 27744447130 scopus 로고    scopus 로고
    • note
    • FPMB tags have been previously employed for the synthesis of discodermolide [ref 1d] and murisolin analogues [ref 10a].
  • 22
    • 27744484677 scopus 로고    scopus 로고
    • note
    • The prefix M denotes mixture of fluorous-tagged compounds.
  • 27
    • 27744471343 scopus 로고    scopus 로고
    • note
    • Fluorous compounds and FluoroFlash silica gel were purchased from Fluorous Technologies, Inc. (www.fluorous.com). D.P.C. holds an equity interest in the company.
  • 32
    • 27744565931 scopus 로고    scopus 로고
    • note
    • The other two fractions (SSR-17 and RSR-17) obtained during this demixing were contaminated with diol by partial deprotection of the TBS group. The source of this deprotection was not investigated.
  • 35
    • 0030987922 scopus 로고    scopus 로고
    • Booth, R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882-4886. PS-trisamine was purchased from Argonaut Technologies (www.argotech.com).
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4882-4886
    • Booth, R.J.1    Hodges, J.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.