Total Synthesis of the Euphorbia Diterpenoid Pepluacetal DOI
Meng Liu,

Chuanhua Wu,

Xingang Xie

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(21)

Published: March 21, 2024

Abstract The first total synthesis of the Euphorbia diterpenoid pepluacetal is disclosed in both racemic and chiral fashions. strategically relies on a photo‐induced Wolff rearrangement/lactonization cascade (WRLC) reaction to access cyclobutane moiety, ring‐closing metathesis/cyclopropanation sequence rapidly forge 7–3 bicyclic system, late‐stage Rh‐catalyzed transannular carbenoid insertion C(sp 3 )−H bond followed by Baeyer–Villiger oxidation ring‐opening manipulations install side chain. synthetic route demonstrates excellent stereochemical control non‐classical concave‐face formation, remote traceless relay high scalability provide 20 mg (+)‐pepluacetal.

Language: Английский

Total Synthesis of the Euphorbia Diterpenoid Pepluacetal DOI
Meng Liu,

Chuanhua Wu,

Xingang Xie

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(21)

Published: March 21, 2024

The first total synthesis of the Euphorbia diterpenoid pepluacetal is disclosed in both racemic and chiral fashions. strategically relies on a photo-induced Wolff rearrangement/lactonization cascade (WRLC) reaction to access cyclobutane moiety, ring-closing metathesis/cyclopropanation sequence rapidly forge 7-3 bicyclic system, late-stage Rh-catalyzed transannular carbenoid insertion C(sp

Language: Английский

Citations

4
Total Synthesis of the Euphorbia Diterpenoid Pepluacetal DOI
Meng Liu,

Chuanhua Wu,

Xingang Xie

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(21)

Published: March 21, 2024

Abstract The first total synthesis of the Euphorbia diterpenoid pepluacetal is disclosed in both racemic and chiral fashions. strategically relies on a photo‐induced Wolff rearrangement/lactonization cascade (WRLC) reaction to access cyclobutane moiety, ring‐closing metathesis/cyclopropanation sequence rapidly forge 7–3 bicyclic system, late‐stage Rh‐catalyzed transannular carbenoid insertion C(sp 3 )−H bond followed by Baeyer–Villiger oxidation ring‐opening manipulations install side chain. synthetic route demonstrates excellent stereochemical control non‐classical concave‐face formation, remote traceless relay high scalability provide 20 mg (+)‐pepluacetal.

Language: Английский

Citations

0