An Efficient and General Method for the Synthesis of α,ω-Difunctional Reduced Polypropionates by Zr-Catalyzed Asymmetric Carboalumination: Synthesis of the Scyphostatin Side Chain

A decrease in the number of linear synthetic steps and an increase in efficiency have been realized in the synthesis of the side chain of scyphostatin. An efficient and selective synthesis of α,ω‐difunctional reduced polypropionates from methyl 3‐hydroxy‐2‐methylpropionate through the use of a Zr‐ca...

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Published inAngewandte Chemie (International ed.) Vol. 43; no. 22; pp. 2911 - 2914
Main Authors Tan, Ze, Negishi, Ei-ichi
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 24.05.2004
WILEY‐VCH Verlag
Wiley
Subjects
Aluminum - chemistry
Amides - chemical synthesis
Amides - chemistry
carboalumination
Carbon - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
enantioselectivity
homogeneous catalysis
Molecular Conformation
Physical Sciences
Polymers - chemical synthesis
Propionates - chemical synthesis
Pyrones - chemical synthesis
Pyrones - chemistry
Science & Technology
Stereoisomerism
synthesis design
zirconium
Zirconium - chemistry
enantioselectivity
ROUTE
ENANTIOSELECTIVE SYNTHESIS
ALKYLALUMINATION
BORRELIDIN
PROTOCOL
CONVENIENT
IONOMYCIN
homogeneous catalysis
carboalumination
FRAGMENT
MONOSUBSTITUTED ALKENES
zirconium
DERIVATIVES
synthesis design
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Summary:A decrease in the number of linear synthetic steps and an increase in efficiency have been realized in the synthesis of the side chain of scyphostatin. An efficient and selective synthesis of α,ω‐difunctional reduced polypropionates from methyl 3‐hydroxy‐2‐methylpropionate through the use of a Zr‐catalyzed asymmetric carboalumination has been developed (see scheme, TBS=tert‐butyldimethylsilyl).
Bibliography:ark:/67375/WNG-BS2ZVPHK-H
ArticleID:ANIE200353429
istex:BB00914B4242B7B50633E112D24DB6786A8140CF
We thank the National Institutes of Heath (grant no. GM36792) and Purdue University for their support of this research, and Boulder Scientific Co. for assistance in the procurement of Zr compounds. The collaborative efforts of B. Liang, T. Novak, and M. Magnin-Lachaux are acknowledged.
We thank the National Institutes of Heath (grant no. GM36792) and Purdue University for their support of this research, and Boulder Scientific Co. for assistance in the procurement of Zr compounds. The collaborative efforts of B. Liang, T. Novak, and M. Magnin‐Lachaux are acknowledged.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200353429