[reaction: see text] Development of new organosilane reagents bearing C-centered chirality where the stereocenter is fully substituted, and their use in the stereocontrolled synthesis of cis- and trans-dihydropyrans containing a trisubstituted olefin is described. The reagents participate in Lewis acid promoted [4+2]-annulations providing useful levels of selectivity with both aliphatic and aromatic aldehydes. A stereoselective synthesis of the C1a-C10 fragment of kendomycin (1) is also described.
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Total synthesis of (-)-kendomycin.
Org Lett
September 2008
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
An enantioselective synthesis of (-)-kendomycin is described and is based on the application of the organosilane-based [4 + 2]-annulation strategy for the assembly of the C1a-C10 fragment. An underutilized samarium(II) iodide-assisted cyclization (intramolecular Barbier-type reaction) is employed to afford the protected macrocycle.
View Article and Find Full Text PDFStereocontrolled [4+2]-annulation accessing dihydropyrans: synthesis of the C1a-C10 fragment of kendomycin.
Org Lett
April 2005
Department of Chemistry and Center for Chemical Methodology and Library Development, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
[reaction: see text] Development of new organosilane reagents bearing C-centered chirality where the stereocenter is fully substituted, and their use in the stereocontrolled synthesis of cis- and trans-dihydropyrans containing a trisubstituted olefin is described. The reagents participate in Lewis acid promoted [4+2]-annulations providing useful levels of selectivity with both aliphatic and aromatic aldehydes. A stereoselective synthesis of the C1a-C10 fragment of kendomycin (1) is also described.
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