Amino-Claisen rearrangements of N-vinylisoquinuclidines in novel approaches to the synthesis of hydroisoquinolines and hydrophenanthridines

Mariano, Patrick S.; Dunaway‐Mariano, Debra; Huesmann, Peter L.

doi:10.1021/jo01315a028

Cited by 37 publications

(12 citation statements)

References 15 publications

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“…(2S*,4afl*,5S*,8aJZ*)-l-Benzyl-2-(l-propyl)-(A-3,4)-5hydroxy-7-oxooctahydroquinoline (14). To a solution of ketone 6b (206 mg, 0.49 mmol) in CH2C12 (5 mL) was added 85% HBF4-Et20 (0.55 mL) and the reaction stirred at ambient temperature for 21 h. The mixture was then shaken for 2 min with 10% HC1 (15 mL), basified with 15% KOH, and extracted with CH2C12.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Stereospecific total syntheses of decahydroquinoline alkaloids (.+-.)-195A and (.+-.)-2-epi-195A

Polniaszek¹,

Dillard²

1992

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

“…The reaction was stirred at 0 °C for 2 h, warmed to ambient temperature and stirred 1 h and then filtered through a glass frit. The filtrate was concentrated to a brown oil which was flash chromatographed on silica gel with a gradient of hexane to 10:90 EtOAc-hexane affording 61 mg (46% from 14) of an oil: ER (NaCl) 1692 (w), 1417 (s) cm"1;…”

Section: Methodsmentioning

confidence: 99%

Stereospecific total syntheses of decahydroquinoline alkaloids (.+-.)-195A and (.+-.)-2-epi-195A

Polniaszek¹,

Dillard²

1992

J. Org. Chem.

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“…These displayed similar spectroscopic data to the earlier analogues 2a and 4a, although the absence of the trifluoro group simplified the NMR data. In the 13C spectrum the CCI 3 moiety was not so far downfield as the CF 3 group (Mariano et al, 1979) (3 96 vs. 126), although it displayed a somewhat larger phosphorus coupling (11 Hz) than any other phosphorus-coupled atom.…”

Section: Resultsmentioning

confidence: 91%

Synthesis and Biological Evaluation of Haloalkyl Phosphate Triester Derivatives of araA and araC

McGuigan

Jones

Tollerfield

et al. 1992

Antivir Chem Chemother

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SummaryNovel phosphate triester derivatives of the antiviral drug araA and the anti-leukaemic agent araC have been prepared as membrane-soluble pro-drugs of the bio-active free nucleotides. In particular, novel trichloro-and trifluoroethyl phosphates have been prepared using phosphorochloridate chemistry, and are fully characterized. An in vitro assay indicates inhibition, by each of the compounds, of thymidine incorportion by mammalian epithelial cells. It is notable that the trichloroethyl derivative is most active in each case, and in the case of araC its activity appears to exceed that of the parent nucleoside.

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“…Some heteroatomic species that are known to undergo [3,3]-sigmatropic rearrangement are zwitterions (8, 1 1-15), ammonium ions (30), and neutral maleates (3 1, 32).…”

Section: Resultsmentioning

confidence: 99%

The reactions of simple dimethylallylamines with dimethyl acetylenedicarboxylate. Formation of 1-dimethylamino-2-allylmaleates via formal allyl transfer

Schwan¹,

Warkentin²

1988

Can. J. Chem.

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. Can. J. Chem. 66, 1686 (1988). Tertiary amines bearing two methyl groups and an allylic substituent (X) react with dimethyl acetylenedicarboxylate (DMAD) to afford the corresponding 1-dimethylamino-2-X' maleates, in which X' is the allylic isomer of X. The mechanism postulated involves reversible formation of a zwitterion by attack of the amine at an sp-carbon of DMAD. The zwitterion then undergoes intramolecular allyl transfer, through a 6-membered transition state. Evidence for a zwitterionic intermediate (quaternary ammonium allenolate) includes capture of the allenolate centre by intramolecular addition to a carbonyl group and by proton transfer from chloroform. ADRIAN L. SCHWAN et JOHN WARKENTIN. Can. J. Chem. 66, 1686 (1988). Les amines tertiaires qui portent deux groupements mCthyles et un substituant allylique (X) rtagissent avec I'acCtyltnedicarboxylate de dimCthyle (ADDM) pour fournir les maleates correspondants, dimtthylamino-l XI-2 malCates, dans lesquels le groupement X' est I'isomkre allylique de X. Le mecanisme postulC implique la formation reversible d'un zwitterion par I'attaque de I'amine sur le carbone-sp de I'ADDM. Le zwitterion subit alors un transfert allylique intramoleculaire par le biais d'un Ctat de transition a six chainons. Les donntes supportant I'hypothkse de I'existence d'un zwitterion comme intermediaire (allknolate d'ammonium quaternaire) comportent la capture du centre allbnolate par une addition intramoleculaire sur un groupement carbonyle ainsi qu'un transfert de proton B partir du chloroforme.[Traduit par la revue]

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Amino-Claisen rearrangements of N-vinylisoquinuclidines in novel approaches to the synthesis of hydroisoquinolines and hydrophenanthridines

Cited by 37 publications

References 15 publications

Stereospecific total syntheses of decahydroquinoline alkaloids (.+-.)-195A and (.+-.)-2-epi-195A

Stereospecific total syntheses of decahydroquinoline alkaloids (.+-.)-195A and (.+-.)-2-epi-195A

Synthesis and Biological Evaluation of Haloalkyl Phosphate Triester Derivatives of araA and araC

The reactions of simple dimethylallylamines with dimethyl acetylenedicarboxylate. Formation of 1-dimethylamino-2-allylmaleates via formal allyl transfer

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