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The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid

Masesane IB, Batsanov AS, Howard JA, Mondal R, Steel PG - Beilstein J Org Chem (2006)

Bottom Line: The nitro oxanorbornene adduct derived from the Diels-Alder reaction of ethyl (E)-3-nitroacrylate and furan provides a versatile template for the stereoselective synthesis of hydroxylated derivatives of 2-aminocyclohexanecarboxylic acid (ACHC).

Affiliation: Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK. masesane@mopipi.ub.bw

ABSTRACT

The nitro oxanorbornene adduct derived from the Diels-Alder reaction of ethyl (E)-3-nitroacrylate and furan provides a versatile template for the stereoselective synthesis of hydroxylated derivatives of 2-aminocyclohexanecarboxylic acid (ACHC).

Reagents: i. HClO4, H2O/acetone; v. Ac2O, pyridine; iii. H2, Pd/C, 24 71%, 25 67%, 26 71%
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C5: Reagents: i. HClO4, H2O/acetone; v. Ac2O, pyridine; iii. H2, Pd/C, 24 71%, 25 67%, 26 71%

Mentions: Similar treatment of epoxides 11 and 13 then afforded the corresponding anti 4,5 diols. Subsequent reduction of the double bond gave the anti-syn-anti-anti and anti-syn-syn-anti isomers 25 and 26 as the only detectable products, Scheme 5. In each case it is noteworthy that the reduction proceeded with delivery of hydrogen to the same face as that occupied by the carbamate and opposite to the 3-acetoxy group. As previously, the stereochemical relationships were initially assigned on the basis of 2D NMR experiments, particularly NOESY. Subsequently, the structure of 26 was confirmed by X-ray crystallographic analysis.

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The oxanorbornene approach to 3-hydroxy, 3,4-dihydroxy and 3,4,5-trihydroxy derivatives of 2-aminocyclohexanecarboxylic acid

Masesane IB, Batsanov AS, Howard JA, Mondal R, Steel PG - Beilstein J Org Chem (2006)

Reagents: i. HClO4, H2O/acetone; v. Ac2O, pyridine; iii. H2, Pd/C, 24 71%, 25 67%, 26 71%
© Copyright Policy - open-access
C5: Reagents: i. HClO4, H2O/acetone; v. Ac2O, pyridine; iii. H2, Pd/C, 24 71%, 25 67%, 26 71%
Mentions: Similar treatment of epoxides 11 and 13 then afforded the corresponding anti 4,5 diols. Subsequent reduction of the double bond gave the anti-syn-anti-anti and anti-syn-syn-anti isomers 25 and 26 as the only detectable products, Scheme 5. In each case it is noteworthy that the reduction proceeded with delivery of hydrogen to the same face as that occupied by the carbamate and opposite to the 3-acetoxy group. As previously, the stereochemical relationships were initially assigned on the basis of 2D NMR experiments, particularly NOESY. Subsequently, the structure of 26 was confirmed by X-ray crystallographic analysis.

Bottom Line: The nitro oxanorbornene adduct derived from the Diels-Alder reaction of ethyl (E)-3-nitroacrylate and furan provides a versatile template for the stereoselective synthesis of hydroxylated derivatives of 2-aminocyclohexanecarboxylic acid (ACHC).

Affiliation: Department of Chemistry, University of Durham, South Road, Durham, DH1 3LE, UK. masesane@mopipi.ub.bw

ABSTRACT

The nitro oxanorbornene adduct derived from the Diels-Alder reaction of ethyl (E)-3-nitroacrylate and furan provides a versatile template for the stereoselective synthesis of hydroxylated derivatives of 2-aminocyclohexanecarboxylic acid (ACHC).

View Similar Images In: Results  - Collection
View Article: PubMed Central - HTML -  PubMed
Show All Figures - Show MeSH
getmorefigures.php?pmc=1524792&rFormat=json&query=null&req=5