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Faulkner, D.J.3
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Kashman, Y.2
Loya, S.3
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Tsukamoto, S.; Kato, H.; Hirota, H.; Fusetani, N. J. Nat. Prod. 1997, 60, 126-130.
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Fusetani, N.1
Sugano, M.2
Matsunaga, S.3
Hashimoto, K.4
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8
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4344628105
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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
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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.
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J. Nat. Prod.
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Andersen, R.J.1
Ireland, C.M.2
Molinski, T.F.3
Bewley, C.B.4
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9
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24944538806
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Gung, B. W.; Gibeau, C.; Jones, A. Tetrahedron: Asymmetry 2005, 16, 3107-3114.
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Tetrahedron: Asymmetry
, vol.16
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Gung, B.W.1
Gibeau, C.2
Jones, A.3
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10
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9944257942
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Gung, B. W.; Gibeau, C.; Jones, A. Tetrahedron: Asymmetry 2004, 15, 3973-3977.
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Tetrahedron: Asymmetry
, vol.15
, pp. 3973-3977
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Gung, B.W.1
Gibeau, C.2
Jones, A.3
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11
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2142858450
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Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
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Ohtani, I.1
Kusumi, T.2
Kashman, Y.3
Kakisawa, H.4
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15
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79851482852
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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)
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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).
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16
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0000006931
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Gonnella, N. C.; Nakanishi, K.; Martin, V. S.; Sharpless, K. B. J. Am. Chem. Soc. 1982, 104, 3775-3776.
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Gonnella, N.C.1
Nakanishi, K.2
Martin, V.S.3
Sharpless, K.B.4
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17
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0037054316
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Molinski, T. F.; Brzezinski, L. J.; Leahy, J. W. Tetrahedron: Asymmetry 2002, 13, 1013-1016.
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(2002)
Tetrahedron: Asymmetry
, vol.13
, pp. 1013-1016
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Molinski, T.F.1
Brzezinski, L.J.2
Leahy, J.W.3
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18
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0030882926
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Schneider, C.; Schreier, P.; Humpf, H. U. Chirality 1997, 9, 563-567.
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(1997)
Chirality
, vol.9
, pp. 563-567
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Schneider, C.1
Schreier, P.2
Humpf, H.U.3
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20
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17644391710
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Naito, J.; Yamamoto, Y.; Akagi, M.; Sekiguchi, S.; Watanabe, M.; Harada, N. Monatsh. Chem. 2005, 136, 411-445.
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(2005)
Monatsh. Chem.
, vol.136
, pp. 411-445
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Naito, J.1
Yamamoto, Y.2
Akagi, M.3
Sekiguchi, S.4
Watanabe, M.5
Harada, N.6
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21
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79851469883
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max 239 (e = 65 000), respectively
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max 239 (e = 65,000), respectively.
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22
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79851495155
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Note that the remote C10-C14 diyne chromophore is "CD silent"
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Note that the remote C10-C14 diyne chromophore is "CD silent".
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23
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79851485149
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Ph.D. Dissertation, University of California, San Diego, La Jolla, CA, November
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Skepper, C. K. Marine Derived Heterocycles. Ph.D. Dissertation, University of California, San Diego, La Jolla, CA, November, 2009.
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(2009)
Marine Derived Heterocycles
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Skepper, C.K.1
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24
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34247112862
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Supporting information of
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Supporting information of Skepper, C. K.; MacMillan, J. B.; Zhou, G. X.; Masuno, M. N.; Molinski, T. F. J. Am. Chem. Soc. 2007, 129, 4150-4151.
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(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 4150-4151
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Skepper, C.K.1
MacMillan, J.B.2
Zhou, G.X.3
Masuno, M.N.4
Molinski, T.F.5
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25
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79851498954
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The configuration of the secondary alcohol 14 was verified using the modified Mosher's method.11
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The configuration of the secondary alcohol 14 was verified using the modified Mosher's method.11
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26
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79851493746
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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).
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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).
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27
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79851498138
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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
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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.
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28
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79851487608
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Insufficient sample of 4a-c remained to apply the ene-diyne naphthoate ECCD method
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Insufficient sample of 4a-c remained to apply the ene-diyne naphthoate ECCD method.
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29
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79851495574
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The unnatural (S) enantiomer of siphonodiol 2 is depicted in ref 1
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The unnatural (S) enantiomer of siphonodiol 2 is depicted in ref 1.
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30
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79851477338
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Systema Porifera; Hooper, J., Van Soest, R. W. M., Eds.; Kluwer/Plenum: New York
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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.
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(1886)
Family Spirastrellidae Ridley & Dendy
, vol.1
, pp. 1994
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Rützler, K.1
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31
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65649141701
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Submilligram yields were determined using quantitation by solvent 13C satellite (QSCS)
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Submilligram yields were determined using quantitation by solvent 13C satellite (QSCS). Dalisay, D. S.; Molinski, T. F. J. Nat. Prod. 2009, 72, 739-744.
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(2009)
J. Nat. Prod.
, vol.72
, pp. 739-744
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Dalisay, D.S.1
Molinski, T.F.2
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32
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33748238501
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Ikemoto, N.; Lo, L.-C.; Nakanishi, K. Angew. Chem., Int. Ed. 1992, 31, 890-891.
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(1992)
Angew. Chem., Int. Ed.
, vol.31
, pp. 890-891
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Ikemoto, N.1
Lo, L.-C.2
Nakanishi, K.3
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