Total synthesis of woodrosin I - Part 2: Final stages involving RCM and an orthoester rearrangement

Chemistry - A European Journal

Volumn 9, Issue 1, 2003, Pages 320-326

  Fürstner, Alois ^a   Jeanjean, Fabien ^a   Razon, Patrick ^a   Wirtz, Conny ^a   Mynott, Richard ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

Glycosides; Metathesis; Natural products; Oligosaccharides; Ruthenium

Indexed keywords

CATALYSTS; ESTERS; HYDROGENATION; LIPIDS; RESINS; SUGARS;

GRUBBS CARBENE COMPLEX;

SYNTHESIS (CHEMICAL);

ALKADIENE; ALKENE; CARBENE; ESTER; GLUCOSIDE; GLYCOSIDE; OLIGOSACCHARIDE; POLYSACCHARIDE; RUTHENIUM COMPLEX; TRICHLOROACETIMIDIC ACID; UNCLASSIFIED DRUG; WOODROSIN I;

ARTICLE; BIOCHEMISTRY; CARBOHYDRATE ANALYSIS; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMISTRY; COMPLEX FORMATION; DRUG SYNTHESIS; GLYCOSYLATION; HYDROGENATION; METHODOLOGY; MOLECULAR GENETICS; REACTION ANALYSIS; STEREOISOMERISM; SYNTHESIS;

ALKENES; BIOCHEMISTRY; CARBOHYDRATE SEQUENCE; ESTERS; GLUCOSIDES; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

EID: 0037415095     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390026     Document Type: Article

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72. This refers to the geometry of the double bond of a macrocyclic cycloalkene that cannot yet be controlled; for an indirect solution to this problem see: a) A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760; Angew. Chem. Int. Ed. 1998, 37, 1734-1736; b) A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108-11113; c) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5297-5315 and references therein.
73. This refers to the geometry of the double bond of a macrocyclic cycloalkene that cannot yet be controlled; for an indirect solution to this problem see: a) A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760; Angew. Chem. Int. Ed. 1998, 37, 1734-1736; b) A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108-11113; c) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5297-5315 and references therein.
74. This refers to the geometry of the double bond of a macrocyclic cycloalkene that cannot yet be controlled; for an indirect solution to this problem see: a) A. Fürstner, G. Seidel, Angew. Chem. 1998, 110, 1758-1760; Angew. Chem. Int. Ed. 1998, 37, 1734-1736; b) A. Fürstner, O. Guth, A. Rumbo, G. Seidel, J. Am. Chem. Soc. 1999, 121, 11108-11113; c) A. Fürstner, C. Mathes, C. W. Lehmann, Chem. Eur. J. 2001, 7, 5297-5315 and references therein.
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80. For another study on complex glycolipids from this laboratory see: a) A. Fürstner, M. Albert, J. Mlynarski, M. Matheu, J. Am. Chem. Soc. 2002, 124, 1168-1169; b) A. Fürstner. J. Mlynarski, M. Albert, J. Am. Chem. Soc. 2002, 124, 10274-10275.
81. For another study on complex glycolipids from this laboratory see: a) A. Fürstner, M. Albert, J. Mlynarski, M. Matheu, J. Am. Chem. Soc. 2002, 124, 1168-1169; b) A. Fürstner. J. Mlynarski, M. Albert, J. Am. Chem. Soc. 2002, 124, 10274-10275.