118093-03-1Relevant articles and documents
Enantioselective Total Synthesis of Berkeleyone A and Preaustinoids
Franzoni, Ivan,Guo, Chuning,Hong, Benke,Ji, Yunpeng,Jia, Hongli,Li, Houhua,Zhang, Yang
, p. 14869 - 14874 (2021/05/27)
Herein we report the first enantioselective total synthesis of 3,5-dimethylorsellinic acid-derived meroterpenoids (?)-berkeleyone A and its five congeners ((?)-preaustinoids A, A1, B, B1, and B2) in 12–15 steps, starting from commercially available 2,4,6-trihydroxybenzoic acid hydrate. Based upon the recognition of latent symmetry within D-ring, our convergent synthesis features two critical reactions: 1) a symmetry-breaking, diastereoselective dearomative alkylation to assemble the entire carbon core, and 2) a Sc(OTf)3-mediated sequential Krapcho dealkoxycarbonylation/carbonyl α-tert-alkylation to forge the intricate bicyclo[3.3.1]nonane framework. We also conducted our preliminary biomimetic investigations and uncovered a series of rearrangements (α-ketol, α-hydroxyl-β-diketone, etc.) responsible for the biomimetic diversification of (?)-berkeleyone A into its five preaustinoid congeners.
Biomimetic Synthesis of Complex Flavonoids Isolated from Daemonorops “Dragon's Blood”
Schmid, Matthias,Trauner, Dirk
, p. 12332 - 12335 (2017/09/25)
The dragonbloodins are a pair of complex flavonoid trimers that have been isolated from the palm tree Daemonorops draco, one of the sources of the ancient resin known as “dragon's blood”. We present a short synthesis that clarifies their relative configur