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Volumn 64, Issue 49, 2008, Pages 11313-11318

Stereocontrolled synthesis of cytotoxic anhydrosphingosine pachastrissamine by using [3.3] sigmatropic rearrangement of allyl cyanate

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETAMIDO 3 O ACETYL 1,4 ANHYDRO 1,3,4 OCTADECANETRIOL; 2 OXO 6 TETRADECYLHEXAHYDROFURO[3,4 D]OXAZOL 4 YL ACETATE; 2,2 DIMETHYL 5 (TETRADEC 2 YNYL) 1,3 DIOXOLAN 4 YL)METHOXY)DIMETHYLSILANE; 2,2 DIMETHYL 5 TETRADECYL 1,3 DIOXOLAN 4 YL)ACRYLALDEHYDE; 2,2 DIMETHYL 5 TETRADECYL 1,3 DIOXOLAN 4 YL)ACRYLATE; 2,2 DIMETHYL 5 TETRADECYL 1,3 DIOXOLAN 4 YL)METHANOL; 2,2 DIMETHYL 5 TETRADECYL 1,3 DIOXOLAN 4 YL)PENT 1 EN 3 OL; 2,2 DIMETHYL 5 TETRADECYL 1,3 DIOXOLAN 4 YL)PENT 2 ENYLCARBAMATE; 2,2 DIMETHYL 5 TETRADECYL 1,3 DIOXOLAN 4 YL)PROP 2 EN 1 OL; 4 (BUT 1 ENYL) 5 (1 HYDROXYPENTADECYL) OXAZOLIDIN 2 ONE; AMINE; CYANIC ACID; PACHASTRISSAMINE; PACHASTRISSAMINE CARBAMATE; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 54549096756     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.036     Document Type: Article
Times cited : (44)

References (39)
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    • For previous syntheses:
    • For previous syntheses:
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    • For a comprehensive review describing the syntheses of pachastrissamine between 2005 and 2007, see:
    • Enders D., Terteryan V., and Palecek J. Synthesis (2008) 2278-2282 For a comprehensive review describing the syntheses of pachastrissamine between 2005 and 2007, see:
    • (2008) Synthesis , pp. 2278-2282
    • Enders, D.1    Terteryan, V.2    Palecek, J.3
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    • 1-Tridecyne was readily prepared in 78% yield from 1-undecanol by the two-step route involving (1) bromination of 1-undecanol by treatment with triphenylphosphine and N-bromosuccinimide in DMF ( ), and (2) the reaction of 1-bromoundecane with lithium acetylide-ethylenediamine complex in DMSO (
    • 1-Tridecyne was readily prepared in 78% yield from 1-undecanol by the two-step route involving (1) bromination of 1-undecanol by treatment with triphenylphosphine and N-bromosuccinimide in DMF (. Bates H.A., Farina J., and Tong M. J. Org. Chem. 51 (1986) 2637-2641 ), and (2) the reaction of 1-bromoundecane with lithium acetylide-ethylenediamine complex in DMSO (
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    • Although TEMPO-catalyzed oxidation of 7 proceeded cleanly, separation of TEMPO from the product 8 was difficult. Use of 4-acetamido-TEMPO circumvented this purification problem. For TEMPO-catalyzed oxidation employing NCS as the oxidant, see:
    • Although TEMPO-catalyzed oxidation of 7 proceeded cleanly, separation of TEMPO from the product 8 was difficult. Use of 4-acetamido-TEMPO circumvented this purification problem. For TEMPO-catalyzed oxidation employing NCS as the oxidant, see:. Einhorn J., Einhorn C., Ratajczak F., and Pierre J.-L. J. Org. Chem. 61 (1996) 7452-7454
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    • note
    • 13C NMR data of v and vi. We thank Ken Okumura for these experiments.{A figure is presented}
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    • In the previous report, we recommended the addition of tributylstannous methoxide as a catalyst to effect the in situ trapping of isocyanates with alcohols. Dibutyltin maleate offers advantages of low cost and ease of purification steps to remove residual organotin byproducts. See:
    • In the previous report, we recommended the addition of tributylstannous methoxide as a catalyst to effect the in situ trapping of isocyanates with alcohols. Dibutyltin maleate offers advantages of low cost and ease of purification steps to remove residual organotin byproducts. See:. Ichikawa Y., Ohara F., Kotsuki H., and Nakano K. Org. Lett. 8 (2006) 5009-5012
    • (2006) Org. Lett. , vol.8 , pp. 5009-5012
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    • Our initial route to 16 involved oxidative cleavage of the alkene moiety in 13 with sodium periodate and a catalytic amount of osmium tetroxide in the presence of 2,6-lutidine (. ). In this case, the subsequent reduction of the resultant products with sodium borohydride in methanol occurred smoothly to afford the diol i in 60% yield over two steps.{A figure is presented}
    • Our initial route to 16 involved oxidative cleavage of the alkene moiety in 13 with sodium periodate and a catalytic amount of osmium tetroxide in the presence of 2,6-lutidine (. Yu W., Mei Y., Kang Y., Hua Z., and Jin Z. Org. Lett. 6 (2004) 3217-3219. ). In this case, the subsequent reduction of the resultant products with sodium borohydride in methanol occurred smoothly to afford the diol i in 60% yield over two steps.{A figure is presented}
    • (2004) Org. Lett. , vol.6 , pp. 3217-3219
    • Yu, W.1    Mei, Y.2    Kang, Y.3    Hua, Z.4    Jin, Z.5
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    • note
    • 1H NMR spectra of our diacetate 17 match those reported by Davies. See Ref. 6q.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.