Synthetic Study of Rubriflordilactone B: Highly Stereoselective Construction of the C-5-epi ABCDE Ring System

Wang, Yong; Li, Zhongle; Lv, Liangbo; Xie, Zhenzhen

doi:10.1021/acs.orglett.6b00057

Cited by 36 publications

(21 citation statements)

References 64 publications

(40 reference statements)

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“…[9a-e] Rubriflordilactone B (4)i sabisnortriterpenoid featuring at etrasubstituted arene moiety,and was isolated by Sun et al from Schisandra rubriflora along with its congener rubriflordilactone A(3). [10] The structures of both compounds were determined by X-ray crystallography.R ecently,t he synthesis of 3 was independently achieved by us [6a] and Anderson et al, [9g] but endeavors [11,12] towards the synthesis of 4 have not been successful. Right before we submitted this manuscript, Xie et al reported an elegant synthesis of at runcated model of 4 with the undesired configuration at the C5 position by ar hodiumcatalyzed [2+ +2+ +2] cycloaddition.…”

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confidence: 99%

Total Synthesis of Rubriflordilactone B

et al. 2016

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Taking advantage of a 6π electrocyclization-aromatization strategy, we accomplished the first and asymmetric total synthesis of rubriflordilactone B, a heptacyclic Schisandraceae bisnortriterpenoid featuring a tetrasubstituted arene moiety. The left-hand fragment was accessed through a chiral-pool-based route, and linked to the right-hand fragment by a Sonogashira coupling. The cis geometry of the electrocyclization substrates was established by hydrogenation or hydrosilylation of the alkyne. An electrocyclization-aromatization sequence finally built the multisubstituted arene. The hydrosilylation approach was of significant advantage in terms of reaction scale, reproducibility, and intermediate stability. The structure of synthetic rubriflordilactone B was validated by X-ray crystallographic analysis, and found to be consistent with that reported for the authentic natural product based on an independent X-ray crystallographic analysis. However, obvious differences in the NMR spectra of the synthetic and authentic samples suggest that the authentic samples subjected to X-ray crystallography and NMR spectroscopy were two different compounds.

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confidence: 99%

Total Synthesis of Rubriflordilactone B

et al. 2016

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“…[92] The importantb iological activity of (+ +)-compactin hasled to the publication of severalsynthesis. [94] The authors carriedo ut as creening of known iminium/enamine type catalysts (prolined erivatives and MacMillan catalyst 160). [94] The authors carriedo ut as creening of known iminium/enamine type catalysts (prolined erivatives and MacMillan catalyst 160).…”

Section: Organocatalytic Mukaiyama-michael Reactions 41 Imidazolidimentioning

confidence: 99%

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

Frías

Cieślik

Fraile

et al. 2018

Chemistry A European J

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Organocatalysis is a growing area that is benefiting from advances in many fields. Its implementation has begun in areas such as supramolecular chemistry, organic chemistry and natural product synthesis. While a considerable number of important publications in the field of organocatalytic Mukaiyama-type additions have been reported, they are yet to be fully covered in a review. Therefore, we would like to highlight the applications of various kinds of organocatalysts in Mukaiyama-type reactions, while also including the vinylogous Mukaiyama variation. Herein we describe and discuss the development and current state of the art of the organocatalytic Mukaiyama reaction, vinylogous Mukaiyama and related reactions.

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“…[45] Zuerst wurden mittels Mukaiyama-Michael-Reaktion zwischen dem Silyloxyfuran 110 und dem Aldehyd 111 die benachbarten C5-und C10-Stereozentren realisiert. [45] Zuerst wurden mittels Mukaiyama-Michael-Reaktion zwischen dem Silyloxyfuran 110 und dem Aldehyd 111 die benachbarten C5-und C10-Stereozentren realisiert.…”

Section: Ansätze Fürd As Aromatische D-ringfragmentunclassified

“…Bisher wurden drei Fragmentsyntheseansätze fürn ichtaromatische 7,6,5-fusionierte Tricyclen verçffentlicht, [36][37][38] außerdem entwickelten Yang und Mitarbeiter eine Totalsynthese von Propindilacton G. [39][40][41][42] Bezüglich der Aromatenreihe stand der Aufbau des hochgradig substituierten D-Rings,der in den Rubriflordilactonen Aund B(4 und 9)enthalten ist, im Fokus der Aufmerksamkeit. [20,[43][44][45] Diese Bemühungen gipfelten in drei Totalsynthesen. [33,46,47] 2.2.1.…”

Section: Schiartane:s Yntheseansätze Fürd Ie Herstellung Von Fragmentunclassified

“…Xie und Te am entwickelten 2016 auf der Basis einer Rhodium-katalysierten [2+ +2+ +2]-Cyclisierung einen ähnlichen Ansatz fürR ubriflordilacton B( 9)( Schema 16). [45] Zuerst wurden mittels Mukaiyama-Michael-Reaktion zwischen dem Silyloxyfuran 110 und dem Aldehyd 111 die benachbarten C5-und C10-Stereozentren realisiert. [50] Der Aldehyd 113 wurde dann in fünf Schritten weiter zum Tr iin 116 umgesetzt.…”

Section: Ansätze Fürd As Aromatische D-ringfragmentunclassified

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Schinortriterpenoide: eine Fallstudie in Synthesedesign

Cheong

Carter

2017

Angewandte Chemie

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Die Identifikationsnummer(ORCID) eines Autors ist unter http://dx. Kurzaufsätze 1730 www.angewandte.deSchema 4. Ghoshs Doppel-RCM-Ansatz fürdas ABC-Ringsystem. AIBN = a,a'-Azobisisobutyronitril, DMSO = Dimethylsulfoxid, NBS = N-Bromsuccinimid. Schema 5. Yangs Claisen-Umlagerungsansatz fürdas CD-Ringsystem. Cp = Cyclopentadienyl, DMP = Dess-Martin-Periodinan, Trisyl = 2,4,6-Triisopropylbenzensulfonyl. Schema 6. Paquettes Pinakolmakrocyclisierungsansatz fürdas CD-Ringsystem. 9-BBN = 9-Borabicyclononan, DMF = N,N-Dimethylformamid, dppf = 1,1'-Ferrocendiyl-bis(diphenylphosphin), HMPA = Hexamethylphosphoramid, IBX = 2-Iodoxybenzoesäure, mCPBA = meta-Chlorperoxybenzoesäure, Tf = Trifluormethansulfonyl. Angewandte Chemie Kurzaufsätze Schema 14. Andersons Palladium-oder Cobalt-katalysierter [2+ +2+ +2]-Cyclisierungsansatz fürdas CDE-Ringsystem. Schema 15. Ghoshs Diels-Alder/Oxidationsansatz im Eintopfverfahren fürdas CD-Ringsystem. Schema 16. Xies Rhodium-katalysierter [2+ +2+ +2]-Cyclisierungsansatz fürdas ABCDE-Ringsystem. DCE = 1,2-Dichlorethan, DNBA = 2,4-Dinitrobenzoesäure. Angewandte Chemie Kurzaufsätze

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Synthetic Study of Rubriflordilactone B: Highly Stereoselective Construction of the C-5-epi ABCDE Ring System

Cited by 36 publications

References 64 publications

Total Synthesis of Rubriflordilactone B

Total Synthesis of Rubriflordilactone B

Development and Application of Asymmetric Organocatalytic Mukaiyama and Vinylogous Mukaiyama‐Type Reactions

Schinortriterpenoide: eine Fallstudie in Synthesedesign

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