Asymmetric total syntheses of spisulosine, its diastereo- and regio-isomers

Starting from palmityl alcohol, divergent stereoselective syntheses of spisulosine and its diastereo- and regio-isomers have been achieved. In the Sharpless asymmetric dihydroxylation-based approach, the key step is the synthesis of monoprotected diol, whereas Miyashita’s boron-directed C-2 regiosel...

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Bibliographic Details
Published inTetrahedron Vol. 66; no. 47; pp. 9304 - 9309
Main Authors Dinda, Subal Kumar, Das, Sajal Kumar, Panda, Gautam
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.11.2010
Elsevier
Subjects
Aliphatic compounds
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
RMHGERRKGNCIBM-QZTJIDSGSA-N
XYRSTKMIVCIDBU-PMACEKPBSA-N
FFCUICJNIDUBJF-WOJBJXKFSA-N
YRYJJIXWWQLGGV-ROUUACIJSA-N
XYRSTKMIVCIDBU-VQTJNVASSA-N
YZFWQAZFXICNNE-QZTJIDSGSA-N
YRYJJIXWWQLGGV-ZWKOTPCHSA-N
FFCUICJNIDUBJF-UXHICEINSA-N
KPWMATOTRWJGRX-VQTJNVASSA-N
VNCXVYSZNAOYNP-RBUKOAKNSA-N
KPWMATOTRWJGRX-WOJBJXKFSA-N
YNRMONDLMYVLJR-MSOLQXFVSA-N
KILDFXLCSAZVOM-LOSJGSFVSA-N
MVWUXBRAWRAIHP-QZTJIDSGSA-N
RMHGERRKGNCIBM-ZWKOTPCHSA-N
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AGENT
REGIOCHEMICAL CONTROL
2,3-EPOXY ALCOHOLS
CHELATING PROCESSES
ES-285
RING-OPENING REACTIONS
1,2-EPOXIDES
Protecting group
Diol
Aminoalcohol
Regioselectivity
Organic azide
Long chain
Sharpless epoxidation
Alcohol
Organic boron compounds
Oxygen heterocycle
Diastereoselectivity
Total synthesis
Stereoselectivity
Asymmetric synthesis
Sharpless dihydroxylation
Epoxide
Chemical synthesis
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Summary:Starting from palmityl alcohol, divergent stereoselective syntheses of spisulosine and its diastereo- and regio-isomers have been achieved. In the Sharpless asymmetric dihydroxylation-based approach, the key step is the synthesis of monoprotected diol, whereas Miyashita’s boron-directed C-2 regioselective azidolysis of enantiomerically pure epoxy alcohol is the vital step in the Sharpless asymmetric epoxidation-based route. The latter approach involves the first protecting-group-free synthesis of spisulosine. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.09.018