Literature DB >> 10822536

Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-beta-KDO.

S D Burke1, G M Sametz.   

Abstract

[formula: see text] Total syntheses of KDO and 2-deoxy-beta-KDO are reported. The C2-symmetric dienediol 4 was desymmetrized by conversion to its corresponding 1,4-dioxanone 5. Ireland-Claisen rearrangement of 5 provided the 6-vinyldihydropyran-2-carboxylate template 6. Double-Sharpless asymmetric dihydroxylation gave the tetraol 7a, which was converted to KDO and 2-deoxy-beta-KDO using methods similar to those previously reported. This synthetic scheme provides a flexible route to KDO and KDO analogues.

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Year:  1999        PMID： 10822536     DOI： 10.1021/ol9905506

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

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Journal:  J Org Chem       Date:  2008-09-24       Impact factor: 4.354

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Journal:  Org Lett       Date:  2012-09-10       Impact factor: 6.005

4.  Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate.

Authors:  Barry M Trost; Aaron Aponick
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5.  Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C 2-symmetric building block: a strategy for the synthesis of decanolide natural products.

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Journal:  Beilstein J Org Chem       Date:  2013-11-18       Impact factor: 2.883
  5 in total

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