Short, Enantioselective Total Synthesis of Highly Oxidized Taxanes

In the realm of natural product chemistry, few isolates have risen to the level of fame justifiably accorded to Taxol (1) and its chemical siblings. This report describes the most concise route to date for accessing the highly oxidized members of this family. As representative members of taxanes con...

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Bibliographic Details
Published in:Angewandte Chemie 2016-07, Vol.128 (29), p.8420-8424
Main Authors: Yuan, Changxia, Jin, Yehua, Wilde, Nathan C., Baran, Phil S.
Format: Article
Language:English
Subjects:
Chemical synthesis
Chemistry
Enantiomers
Isomerization
Natural products
Naturstoffe
Olefins
Oxidation
Oxidationen
Oxygen atoms
Paclitaxel
Röntgen-Beugung
Siblings
Strategy
Synthesis
Taxane
Taxanes
Taxol
Terpene
Totalsynthesen
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Summary:In the realm of natural product chemistry, few isolates have risen to the level of fame justifiably accorded to Taxol (1) and its chemical siblings. This report describes the most concise route to date for accessing the highly oxidized members of this family. As representative members of taxanes containing five oxygen atoms, decinnamoyltaxinine E (2) and taxabaccatin III (3), have succumbed to enantioselective total synthesis for the first time in only 18 steps from a simple olefin starting material. The strategy holistically mimics nature's approach (two‐phase synthesis) and features a carefully choreographed sequence of stereoselective oxidations and a remarkable redox‐isomerization to set the key trans‐diol present in 2 and 3. This work lays the critical groundwork necessary to access even higher oxidized taxanes such as 1 in a more practical fashion, thus empowering a medicinal chemistry campaign that is not wedded to semi‐synthesis. Ausgehend von einem einfachen Olefin wurden hoch oxidierte natürliche Taxane in einer zweiphasige Terpensynthese erhalten. Somit ist die Grundlage für einen praktischen Zugang zu noch höher oxidierten Taxanen geschaffen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201602235