Synthesis of macrocyclic scaffolds suitable for diversity-oriented synthesis of macrolides

Synthesis of macrocyclic glycal-based scaffolds for diversity-oriented synthesis was studied and demonstrated using macrocyclic enyne ring-closing metathesis. The roles of ring size, alkyne substitution, and orientation relative to the glycal were studied. In all cases, the cyclization showed prefer...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 39; pp. 8132 - 8138
Main Authors Grimwood, Michael E., Hansen, Henrik C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.09.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ENYNE METATHESIS
CHEMISTRY
OLEFIN METATHESIS
FERRIER
STEREOCONTROLLED SYNTHESIS
KINETIC SPIROCYCLIZATION
SKELETAL DIVERSITY
SPIROKETALS
Endo stereoisomer
Ring size
Acetylenic compound
Metathesis
Glycal
Oxygen heterocycle
Macrolide
Enynic compound
Macrocycle
Cyclization
Chemical synthesis
Ethylenic compound
Alkyne
Functional group
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Summary:Synthesis of macrocyclic glycal-based scaffolds for diversity-oriented synthesis was studied and demonstrated using macrocyclic enyne ring-closing metathesis. The roles of ring size, alkyne substitution, and orientation relative to the glycal were studied. In all cases, the cyclization showed preference for the thermodynamically favored endo-mode of closure and a trans-double bond at the ring-closure site, leaving macrocyclic scaffolds all containing multiple orthogonal functional groups available for further diversification. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.07.088