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- Title
Divergent Synthetic Route to Oxidized Benzofulvene Sesquiterpenoids: Protecting‐Group‐Free Total Synthesis of Nicotianasesterpenes A, B, and a Polygonum Sesquiterpenoid.
- Authors
Jeong, Myeonggyo; Lee, Hyunkee; Kim, Gibeom; Jo, Jeyun; Chang, Jae Won; Jung, Jee H.; Suh, Young‐Ger; Yun, Hwayoung
- Abstract
A divergent approach toward the protecting‐group‐free total synthesis of oxidized benzofulvene sesquiterpenoids is described. Highlight of our synthesis includes regio‐ and stereoselective assembly of the common intermediate 9 by the orchestrated application of a Pd(0)‐catalyzed reductive dehalogenation, a solvent‐free methylenation, and a vinylogous Stork enamine aldol condensation in a substrate‐controlled manner. The advanced intermediate 9 was efficiently transformed to nicotianasesterpenes A, B, and a polygonum sesquiterpenoid, respectively.
- Subjects
SESQUITERPENES; POLYGONUM; ALDOL condensation; DEHALOGENATION; STORKS
- Publication
European Journal of Organic Chemistry, 2019, Vol 2019, Issue 39, p6714
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201901351