We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Total Syntheses of Rhodomolleins XX and XXII: A Reductive Epoxide‐Opening/Beckwith–Dowd Approach.
- Authors
Yu, Kuan; Yang, Zhen‐Ning; Liu, Chun‐Hui; Wu, Shao‐Qi; Hong, Xin; Zhao, Xiao‐Li; Ding, Hanfeng
- Abstract
A new TiIII‐mediated reductive epoxide‐opening/ Beckwith–Dowd rearrangement process efficiently assembles the bicyclo[3.2.1]octane framework of highly oxidized grayanane diterpenoids. By incorporation of a Cu(tbs)2‐catalyzed (tbs=N‐tert‐butylsalicylaldiminato) intramolecular cyclopropanation, a diastereoselective oxidative dearomatization‐induced Diels–Alder cycloaddition and a MeReO3‐catalyzed Rubottom oxidation, this approach has enabled the first total syntheses of rhodomolleins XX and XXII in 23 and 22 steps, respectively.
- Subjects
EPOXIDATION; DITERPENES; RING formation (Chemistry); DIELS-Alder reaction; STEREOSELECTIVE reactions
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 25, p8644
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201903349