Formal Synthesis of Gracilamine Using Rh(I)-Catalyzed [3 + 2 + 1] Cycloaddition of 1-Yne-Vinylcyclopropanes and CO.
- Resource Type
- Article
- Authors
- Bose, Sritama; Jun Yang; Zhi-Xiang Yu
- Source
- Journal of Organic Chemistry. 8/5/2016, Vol. 81 Issue 15, p6757-6765. 9p.
- Subject
- Language
- ISSN
- 0022-3263
Reported here is a formal synthesis of gracilamine using Rh(I)-catalyzed [3 + 2 + 1] reaction of yne-VCP (±)-4 and CO. The key reaction gave the cycloadduct (±)-trans-3 with the A-B-C core structure of gracilamine. This advanced intermediate was further transformed to Gao's intermediate (±)-2 via regular transformations to realize the formal synthesis of gracilamine. The present strategy was used to accomplish the asymmetric formal synthesis of gracilamine using chiral substrate (+)-4. [ABSTRACT FROM AUTHOR]