Structure and synthesis of a unique isonitrile lipid isolated from the marine mollusk actinocyclus papillatus

Organic Letters

Volumn 13, Issue 8, 2011, Pages 1897-1899

  Manzo, Emiliano ^a   Carbone, Marianna ^a   Mollo, Ernesto ^a   Irace, Carlo ^b   Di Pascale, Antonio ^b   Li, Yan ^c   Ciavatta, Maria Letizia ^a   Cimino, Guido ^a   Guo, Yue Wei ^c   Gavagnin, Margherita ^a  

^a Istituto di Chimica Biomolecolare (ICB)   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTISONITRILE; LIPID; NITRILE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; ISOLATION AND PURIFICATION; MOLLUSC; SYNTHESIS;

ANIMALS; CIRCULAR DICHROISM; LIPIDS; MOLECULAR STRUCTURE; MOLLUSCA; NITRILES;

EID: 79955422670     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200377w     Document Type: Article

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6. Actisonitrile (1): [α]D -7.0 (c = 0.27, CHCl3); CD (n-hexane) [θ]204 850; IR (liquid film) 2925, 2854, 2140, 1748, 1228 cm-1; 1H NMR values (CDCl3) δ 0.88 (3H, t, J = 7 Hz, H3-16′;), 1.20-1.38 (26H, overlapped multiplets, H2-3′/ H2-15′;), 1.57 (2H, m, H2-2′;), 2.12 (3H, s, OCOCH3), δ 3.48 (2H, app t, J=7 Hz, H2-1′;), 3.63 (2H, m, H2-3), 3.96 (1H, m, H-2), 4.20 (1H, dd, J=11, 7 Hz, H-1a), 4.30 (1H, dd, J=11 and 4 Hz Hz, H-1b); selected 13C NMR (CDCl3) δ 14.1 (C-16′;), 20.6 (COCH3), 29.6 (C-2′;), 53.1 (C-2), 62.7 (C-1), 69.1 (C-3), 72.0 (C-1′;); ESIMSm/z 390(M+Na), 363(M-HCN+Na+;HRESIMScalcd for C22H41NO3Na 390.2984, found 390.2973.
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