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Volumn 76, Issue 3, 2011, Pages 894-901

Faulknerynes A-C from a Bahamian Sponge Diplastrella sp.: Stereoassignment by Critical Application of Two Exciton Coupled CD Methods

Author keywords

[No Author keywords available]

Indexed keywords

BAHAMAS; CD METHOD; CRITICAL APPLICATIONS;

EID: 79851477245     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102188q     Document Type: Article
Times cited : (11)

References (32)
  • 8
    • 4344628105 scopus 로고    scopus 로고
    • The compounds are named in honor of the late D. John Faulkner(1940-2002) a pioneer in marine natural products who described diplynes A-E (ref 1), related polyacetylenic alcohols, and hundreds of other compounds
    • The compounds are named in honor of the late D. John Faulkner (1940-2002) a pioneer in marine natural products who described diplynes A-E (ref 1), related polyacetylenic alcohols, and hundreds of other compounds. Andersen, R. J.; Ireland, C. M.; Molinski, T. F.; Bewley, C. B. J. Nat. Prod. 2004, 67, 1239-1251.
    • (2004) J. Nat. Prod. , vol.67 , pp. 1239-1251
    • Andersen, R.J.1    Ireland, C.M.2    Molinski, T.F.3    Bewley, C.B.4
  • 15
    • 79851482852 scopus 로고    scopus 로고
    • Presumably, for this reason, DMB diesters were chosen for the dibenzoate assignment of 2 to move the bisignate split CE to longer wavelengths (? ̃310 nmand diminish potential interference from diynebenzoate interactions (ref 7)
    • Presumably, for this reason, DMB diesters were chosen for the dibenzoate assignment of 2 to move the bisignate split CE to longer wavelengths (? ̃310 nmand diminish potential interference from diynebenzoate interactions (ref 7).
  • 21
    • 79851469883 scopus 로고    scopus 로고
    • max 239 (e = 65 000), respectively
    • max 239 (e = 65,000), respectively.
  • 22
    • 79851495155 scopus 로고    scopus 로고
    • Note that the remote C10-C14 diyne chromophore is "CD silent"
    • Note that the remote C10-C14 diyne chromophore is "CD silent".
  • 23
    • 79851485149 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of California, San Diego, La Jolla, CA, November
    • Skepper, C. K. Marine Derived Heterocycles. Ph.D. Dissertation, University of California, San Diego, La Jolla, CA, November, 2009.
    • (2009) Marine Derived Heterocycles
    • Skepper, C.K.1
  • 25
    • 79851498954 scopus 로고    scopus 로고
    • The configuration of the secondary alcohol 14 was verified using the modified Mosher's method.11
    • The configuration of the secondary alcohol 14 was verified using the modified Mosher's method.11
  • 26
    • 79851493746 scopus 로고    scopus 로고
    • Generally, the short-wavelength component of the ECCD is obscured (λ< 200 nm) in most allylic benzoates with mono- and disubstituted double bonds. However, this component is red-shifted and may be observable at λ ̃180-200 nm in allylic 2-naphthoates (see ref 16) with tri- and tetra-alkyl substituted double bonds and, of course, in allylic acylates of conjugated dienes (λ>220 nm).
    • Generally, the short-wavelength component of the ECCD is obscured (λ< 200 nm) in most allylic benzoates with mono- and disubstituted double bonds. However, this component is red-shifted and may be observable at λ ̃180-200 nm in allylic 2-naphthoates (see ref 16) with tri- and tetra-alkyl substituted double bonds and, of course, in allylic acylates of conjugated dienes (λ>220 nm).
  • 27
    • 79851498138 scopus 로고    scopus 로고
    • In fact, this is evident from the relative asymmetry of the split CEs in 16 and 5 due to differences of superposed paired propargylicO-DMB-alkyne ECCDs arising from the diyne p-p* transition in 5 versus the red-shifted 7-en-3,5-diyne p-p* transition in 16
    • In fact, this is evident from the relative asymmetry of the split CEs in 16 and 5 due to differences of superposed paired propargylicO-DMB-alkyne ECCDs arising from the diyne p-p* transition in 5 versus the red-shifted 7-en-3,5-diyne p-p* transition in 16.
  • 28
    • 79851487608 scopus 로고    scopus 로고
    • Insufficient sample of 4a-c remained to apply the ene-diyne naphthoate ECCD method
    • Insufficient sample of 4a-c remained to apply the ene-diyne naphthoate ECCD method.
  • 29
    • 79851495574 scopus 로고    scopus 로고
    • The unnatural (S) enantiomer of siphonodiol 2 is depicted in ref 1
    • The unnatural (S) enantiomer of siphonodiol 2 is depicted in ref 1.
  • 30
    • 79851477338 scopus 로고
    • Systema Porifera; Hooper, J., Van Soest, R. W. M., Eds.; Kluwer/Plenum: New York
    • Rützler, K., Family Spirastrellidae Ridley & Dendy, 1886. In Systema Porifera; Hooper, J., Van Soest, R. W. M., Eds.; Kluwer/Plenum: New York, 1994; Vol. 1.
    • (1886) Family Spirastrellidae Ridley & Dendy , vol.1 , pp. 1994
    • Rützler, K.1
  • 31
    • 65649141701 scopus 로고    scopus 로고
    • Submilligram yields were determined using quantitation by solvent 13C satellite (QSCS)
    • Submilligram yields were determined using quantitation by solvent 13C satellite (QSCS). Dalisay, D. S.; Molinski, T. F. J. Nat. Prod. 2009, 72, 739-744.
    • (2009) J. Nat. Prod. , vol.72 , pp. 739-744
    • Dalisay, D.S.1    Molinski, T.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.