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Synfacts 2024; 20(11): 1121
DOI: 10.1055/s-0043-1775139
Synthesis of Natural Products

Total Synthesis of (+)-Strepsesquitriol

Contributor(s):
Erick M. Carreira
,
Héloïse M. A. Colombano
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
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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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