Biomimetische Synthese komplexer Flavonoide isoliert aus <i>Daemonorops</i>‐“Drachenblut”

Schmid, Matthias; Trauner, Dirk

doi:10.1002/ange.201705390

Cited by 13 publications

(3 citation statements)

References 23 publications

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“…As Mn(OAc) 3 is an effective oxidant for enolizable carbonyl compounds, [4] excellent yield of 69 % was obtained using a catalytic amount of Mn(OAc) 3 in this auto-oxidation process. [16] Notably, diastereomer C3-epi-7 could not be isolated using the above reaction conditions. The structures of 7 and 7' were initially determined using NMR spectroscopy and later confirmed by 2D NMR spectroscopy of derivative 23.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C

Zong

Zhu

et al. 2021

Angew Chem Int Ed

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An enantioselective synthetic approach for preparing manginoids and guignardones, two types of biogenetically related meroterpenoids, is reported. This bioinspired and divergent synthesis employs an oxidative 1,3-dicarbonyl radical-initiated cyclization and cyclodehydration of the common precursor to forge the central ring of the manginoids and guignardones, respectively, at a late stage. Key synthetic steps include silica-gel-promoted semipinacol rearrangement to form the 6-oxabicyclo[3.2.1]octane skeleton and the Suzuki-Miyaura reaction of vinyl bromide to achieve fragment coupling. This synthesis protocol enables the asymmetric syntheses of four fungal meroterpenoids from commercially available materials. Figure 1. Representative structures of manginoids and guignardones.

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Section: Methodsmentioning

confidence: 99%

Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C

Zong

Zhu

et al. 2021

Angew Chem Int Ed

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“…To achieve a convergent synthesis, intermediate 9 was assembled through a symmetry‐breaking dearomative alkylation of 7 with bicyclic fragment 10 [13] . Finally, carboxylate 7 would be easily obtained through a successive ortho ‐methylation sequence, starting from commercially available 2,4,6‐trihydroxybenzoic acid hydrate ( 11 ) [14] …”

Section: Figurementioning

confidence: 99%

“…As shown in Scheme 1, we commenced our studies by synthesizing aldehyde 12 following a known 4‐step protocol (Supporting Information, Scheme S1) [14] . Subsequent reduction afforded carboxylate 7 .…”

Section: Figurementioning

confidence: 99%

Enantioselective Total Synthesis of Berkeleyone A and Preaustinoids

Zhang

Franzoni³

et al. 2021

Angew Chem Int Ed

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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.

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Iron‐Catalyzed Synthesis of the Hexahydrocyclopenta[c]furan Core and Concise Total Synthesis of Polyflavanostilbene B

et al. 2018

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The first synthesis of polyflavanostilbene B( 1), which has seven contiguous stereocenters including two quaternary carbon centers,f rom abundant polymeric (À)epicatechin gallate on ag ram scale in three steps without the use of protecting groups is reported. The key transformations of this strategy include ar egioselective and stereoselective substitution of resveratrol to give the 4-derivative of (À)epicatechin 3-gallate and an iron-catalyzed cyclization reaction. The possible radical cyclization mechanism in the formation of the hexahydrocyclopenta[c]furan core is also discussed.

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Biomimetische Synthese komplexer Flavonoide isoliert aus Daemonorops‐“Drachenblut”

Cited by 13 publications

References 23 publications

Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C

Enantioselective Total Syntheses of Manginoids A and C and Guignardones A and C

Enantioselective Total Synthesis of Berkeleyone A and Preaustinoids

Iron‐Catalyzed Synthesis of the Hexahydrocyclopenta[c]furan Core and Concise Total Synthesis of Polyflavanostilbene B

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