Synthesis of an A/B- cis -Fused Cyclopenta[ b ]fluorene (6/5/6/5) Ring System for Embellicine A via the Eight-Membered Silylene-Tethered IMDA Reaction
Abstract
High Resolution Image Download MS PowerPoint Slide The first synthesis of an A/B- cis -fused cyclopenta[ b ]fluorene (6/5/6/5) ring system was successfully achieved via an intramolecular Diels–Alder (IMDA) reaction of an eight-membered silylene-tethered precursor. In this key step, a significant conformational change in the diene moiety was achieved by introducing an eight-membered silylene tether, and the desired A/B- cis -fused tetracyclic compound was obtained with complete stereoselectivity. After several functional group manipulations on the D-ring, a fully elaborate tetracyclic fragment of embellicines was successfully synthesized.
Fields of Study & Subjects
Cyclization and Aryne Chemistry
Organic Chemistry Synthesis Methods
Advanced Synthetic Organic Chemistry
Publication details
- Journal / source
- Organic Letters
- Volume
- 28
- Issue
- 5
- Pages
- 1510–1514
- Publication date
- 27 January 2026
- Language
- EN