SYNTHESIS OF (1<i>R,cis</i>)-2-(3-AMINO-2,2-DIMETHYLCYCLOBUTYL)ETHANOL, A PRECURSOR OF CYCLOBUTANE CARBOCYCLIC NUCLEOSIDES

Borges, João; Fernández, Fernando Nieto; Garcia, X.; Hergueta, Antonio R.; López, Carmen

doi:10.1080/00304949709355201

Cited by 7 publications

(3 citation statements)

References 8 publications

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“…In this context, oxidation of a-pinene produced keto-acid derivative 920, 59 which by treatment with hydroxylamine-O-sulfonic acid followed by a Beckmann rearrangement and subsequent esterification gave N-acetyl amino derivative 921. 341 in 923 with NaIO 4 in the presence of catalytic amounts of RuCl 3 produced carboxylic acid 924 in 44% yield, which upon acidic hydrolysis gave the (1R,3S)-3-amino-2,2-dimethylcyclobutanecarboxylic acid 919 in 74% yield (Scheme 230).…”

Section: Synthesis Of C N A;c Derivativesmentioning

confidence: 97%

Stereoselective synthesis of γ-amino acids

Ordóñez

Cativiela

2007

Tetrahedron: Asymmetry

247

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Section: Synthesis Of C N A;c Derivativesmentioning

confidence: 97%

Stereoselective synthesis of γ-amino acids

Ordóñez

Cativiela

2007

Tetrahedron: Asymmetry

247

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“…The synthesis of [1 R , 5 S ]-2-azapinane ( 5 )11 (Scheme 2) was accomplished in five steps (ca 46–50% overall yield) starting from known acetamide 8 ,12 which was available via the Beckmann rearrangement (H 2 NOSO 3 H, AcOH, reflux, 77–81%] of (−)- cis -pinonic acid ( 6 )12,13 ([α] D = − 94.1° ( c 0.63, CHCl 3 ) [lit 13c. − 93.7 ( c 4.60, CHCl 3 ), lit14.…”

mentioning

confidence: 99%

2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis

2011

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The enantiomeric 2-azapinanes, aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (−)- and (+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement of the pinonic acid oximes, cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAlH4 reductions. The anti stereochemistry of the N-methyl groups in the salts with respect to the gem-dimethyl bridge was established by NOE measurements and by an X-ray diffraction analysis.

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“…6,7 This required prior preparation of the enantiomerically pure amino alcohols 3-5. [8][9][10] In this paper we describe a convenient synthesis of the amino alcohols 6 (a structural isomer of 5) and 7 (a lower homologue of 3-6) starting from readily available (-)-(1S)-b-pinene. Both 6 and 7 can be used as expedient starting materials in the synthesis of new carbocyclic nucleosides.…”

mentioning

confidence: 99%

Synthesis of (1R,3R)-3-[2-(Aminoethyl)-2,2-dimethylcyclobutyl]methanol and (1S,3R)-(3-Amino-2,2-dimethylcyclobutyl)methanol from (+)-Nopinone

Figueira¹,

Blanco²,

Caamaño³

et al. 2000

Synthesis

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The title amino alcohols 6 and 7, which are of interest as intermediates in the synthesis of carbocyclic analogs of nucleosides, were synthesized from (+)-nopinone (8). Ring opening of a-isonitrosonopinone leads to a cyanoester which can be directly reduced to 6. Alternatively, a longer route from the lactam 12, one of the Beckmann rearrangement products of 8, leads also to 6, in a higher overall yield. Besides this the isomeric lactam 13 was transformed, upon hydrolytic opening, oxidative degradation of the lateral chain and reduction, into 7.

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SYNTHESIS OF (1R,cis)-2-(3-AMINO-2,2-DIMETHYLCYCLOBUTYL)ETHANOL, A PRECURSOR OF CYCLOBUTANE CARBOCYCLIC NUCLEOSIDES

Cited by 7 publications

References 8 publications

Stereoselective synthesis of γ-amino acids

Stereoselective synthesis of γ-amino acids

2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis

Synthesis of (1R,3R)-3-[2-(Aminoethyl)-2,2-dimethylcyclobutyl]methanol and (1S,3R)-(3-Amino-2,2-dimethylcyclobutyl)methanol from (+)-Nopinone

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