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Synfacts 2024; 20(11): 1121
DOI: 10.1055/s-0043-1775139
DOI: 10.1055/s-0043-1775139
Synthesis of Natural Products
Total Synthesis of (+)-Strepsesquitriol
Li L.-Z,
Huang Y.-R,
Xu Z.-X,
He H.-S,
Ran H.-W,
Zhu K.-Y,
Han J.-C,
*,
Li C.-C.
*
Southern University of Science and Technology, Shenzhen, P. R. of China
Synthesis of Bridged Five-Membered Ring Systems by Type II [3+2] Annulation of Allenylsilane-ene.
J. Am. Chem. Soc. 2024;
146: 24782-24787
DOI: 10.1021/jacs.4c09384
Synthesis of Bridged Five-Membered Ring Systems by Type II [3+2] Annulation of Allenylsilane-ene.
J. Am. Chem. Soc. 2024;
146: 24782-24787
DOI: 10.1021/jacs.4c09384
Key words
(+)-strepsesquitriol - asymmetric hydrogenation - copper-promoted SN2’ substitution - stereospecific [3+2] annulation - ring-closing metathesis
Significance
Han, Li and co-workers present the first asymmetric total synthesis of (+)-strepsesquitriol. To access the bridged bicyclo[3.2.1]octane ring system, the authors developed a type II intramolecular [3+2] annulation of allenylsilane.
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Comment
The bicyclo[3.2.1]octane H was accessed through stereospecific [3+2] annulation of allenylsilane-ene G. Double Grignard addition followed by ring-closing metathesis afforded the fused system M. Functional group adjustments and global deprotection completed the synthesis of (+)-strepsesquitriol.
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Publication History
Article published online:
16 October 2024
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