Synthesis of 8-Desbromohinckdentine A<sup>1</sup>

Liu, Yahu A.; McWhorter, William W.

doi:10.1021/ja021380m

Cited by 156 publications

(61 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[3][4][5] After screening different reagents and conditions,w ea chieved the synthesis of the C8,C10-dibrominated compound 27 in 75 %yield by performing the bromination of 26 in DMF at 0 8 8Cu sing NBS (2.7 equiv) as the brominating reagent. [3][4][5] After screening different reagents and conditions,w ea chieved the synthesis of the C8,C10-dibrominated compound 27 in 75 %yield by performing the bromination of 26 in DMF at 0 8 8Cu sing NBS (2.7 equiv) as the brominating reagent.…”

Section: Angewandte Chemiementioning

confidence: 99%

“…[2] Total synthesis of the racemic 8-desbromo analogue and the natural product itself have been achieved by the groups of McWhorter [3] and Kawasaki, [4] respectively.A ne legant enantioselective synthesis of (+ +)-hinckdentine A, featuring akey asymmetric dearomative cyclization of functionalized N-acyl tetrahydrocarbazole,h as recently been accomplished by Kitamura, Fukuyama, and coworkers. [2] Total synthesis of the racemic 8-desbromo analogue and the natural product itself have been achieved by the groups of McWhorter [3] and Kawasaki, [4] respectively.A ne legant enantioselective synthesis of (+ +)-hinckdentine A, featuring akey asymmetric dearomative cyclization of functionalized N-acyl tetrahydrocarbazole,h as recently been accomplished by Kitamura, Fukuyama, and coworkers.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Heteroannulation of Arynes with α‐Amino Imides: Synthesis of 2,2‐Disubstituted Indolin‐3‐ones and Application to the Enantioselective Total Synthesis of (+)‐Hinckdentine A

et al. 2018

View full text Add to dashboard Cite

A novel heteroannulation reaction between α-amino imides and in situ generated arynes has been developed for the synthesis of 2,2-disubstituted indolin-3-ones. An enantioselective total synthesis of the marine alkaloid (+)-hinckdentine A was subsequently accomplished using this reaction as a key step. A catalytic enantioselective Michael addition of an α-aryl-α-isocyanoacetate to phenyl vinyl selenone was employed for the construction of the enantioenriched α-quaternary α-amino ester.

show abstract

Section: Angewandte Chemiementioning

confidence: 99%

mentioning

confidence: 99%

Heteroannulation of Arynes with α‐Amino Imides: Synthesis of 2,2‐Disubstituted Indolin‐3‐ones and Application to the Enantioselective Total Synthesis of (+)‐Hinckdentine A

et al. 2018

View full text Add to dashboard Cite

show abstract

“…[8] Alternative approaches to 3-oxindoles are also reported in the literature. [9] Due to the presence of ar igid conjugated electron donoracceptorf ragment restricting intramolecular rotation( RIR), several pseudoindoxyls exhibit fluorescent properties. In 1983, during the isolation of various alkaloids of Aspidospermao blongum,Potier et al isolated pseudoindoxyl derivatives as "Produit jaune, amorphe, trsf luorescent à l'UV".…”

Section: Introductionmentioning

confidence: 99%

Access to 3‐Oxindoles from Allylic Alcohols and Indoles

Lauwick

Sun

Akdas-Kilig

et al. 2018

Chemistry A European J

View full text Add to dashboard Cite

The site-selective and regioselective allylation of 2-substituted indoles was performed by using a ruthenium(IV) precatalyst containing a phosphine-sulfonate chelate. Mono-, di-, and triallylated indoles were selectively obtained depending on the reaction conditions with the formation of water as the only byproduct. The preparation of 3-oxindole derivatives was then successfully performed owing to air oxidation of the corresponding allylated indoles. Diallylated pseudoindoxyls were proven to be good synthons to perform cyclization through a ring-closing metathesis reaction to afford the corresponding tricyclic adducts. The photophysical properties of the 3-oxindoles were measured, and some of the compounds showed strong fluorescence in water.

show abstract

“…McWhorter and coworkers applied an HCO 2 H-promoted rearrangement of the a-tertiary hydroxy imine 269 in the synthesis of 8-desbromohinckdentine A (Scheme 144). 196,197 The stereospecific 1,2-migration of the allyl group afforded indolone 270 with required key C12 quaternary carbon center. After transformation from 270 to the hinckdentine A core 271, the target molecule was obtained by a bromination reaction.…”

Section: Simple Epoxides and 23-epoxy Ketonesmentioning

confidence: 99%