Highly Functionalized Pyranopyrans from Furans:  A Synthesis of the C27−C38 and C44−C53 Subunits of Norhalichondrin B

A synthesis of highly functionalized pyranopyrans based on an Achmatowicz oxidation followed by a remarkably diastereoselective Kishi reduction is described in the context of studies directed toward norhalichondrin B.

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 25; pp. 5299 - 5302
Main Authors Henderson, James A, Jackson, Katrina L, Phillips, Andrew J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.12.2007
Amer Chemical Soc
Subjects
Carbon - chemistry
Chemistry
Chemistry, Organic
Furans - chemical synthesis
Furans - chemistry
Molecular Structure
Oxidation-Reduction
Physical Sciences
Pyrans - chemical synthesis
Pyrans - chemistry
Science & Technology
HALICHONDRIN-B
EXPEDITIOUS SYNTHESIS
F-RING
STEREOSELECTIVE C-GLYCOSYLATION
EFFICIENT SYNTHESIS
CHIRAL SYNTHESIS
ANTITUMOR POLYETHER MACROLIDE
MICHAEL REACTIONS
MARINE SPONGE
NATURAL PRODUCTS
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Summary:A synthesis of highly functionalized pyranopyrans based on an Achmatowicz oxidation followed by a remarkably diastereoselective Kishi reduction is described in the context of studies directed toward norhalichondrin B.
Bibliography:Medline
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ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702559e