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
Key words
(+)-strepsesquitriol - asymmetric hydrogenation - copper-promoted S
N2’ 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.
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.
