- Enantioselective Total Synthesis of Berkeleyone A and Preaustinoids
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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.
- Franzoni, Ivan,Guo, Chuning,Hong, Benke,Ji, Yunpeng,Jia, Hongli,Li, Houhua,Zhang, Yang
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supporting information
p. 14869 - 14874
(2021/05/27)
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- Biomimetic Synthesis of Complex Flavonoids Isolated from Daemonorops “Dragon's Blood”
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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
- Schmid, Matthias,Trauner, Dirk
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supporting information
p. 12332 - 12335
(2017/09/25)
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- Trimethoxyphenyl Compounds, XI. Constituents of Hagenia abyssinica, 2: Synthesis of Phloracylophenones Containing One Phloroglucinol Unit
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For the Koso constituents K6 and K8, we previously proposed the structures 1a, b and 2a, b.These assignments have been confirmed by synthesis. - Keywords: Flores koso, Revised Structure, Synthesis of Phloroglucinols
- Schiemenz, Guenter Paulus,Behrens, Heinz,Ebert, Claus Peter,Maienschein, Konrad,Schroeder, Jens-Michael
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p. 681 - 692
(2007/10/02)
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- Trimethoxyphenyl Compounds, X. Constituents of Hagenia abyssinica, 1: Isolation of Kosins and Structure Elucidation of Phloracylophenones Containing One Phloroglucinol Unit
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From Hagenia abyssinica, 26 compounds were isolated, mostly phloracylophenones with one to three phloroglucinol units.The structure elucidation of three phloracylophenones with one phloroglucinol unit is described. - Keywords: Flores koso, Natural Phlorog
- Schiemenz, Guenter Paulus,Schroeder, Jens-Michael
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p. 669 - 680
(2007/10/02)
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