The stereochemistry of palladium- and platinum-catalyzed hydrogenations of nitro sugar epoxides

Baer, Hans H.; Madumelu, Chukwuemeka B.; Hanna, Zaher S.; Potvin, Pierre

doi:10.1016/0008-6215(79)80014-2

Cited by 15 publications

References 47 publications

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Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 0^2,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives

Nativi

Reymond

Vogel

1989

Helvetica Chimica Acta

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Ethyl and tert-butyl azidoformdte added to 7-oxabicyclo[2.2.l]hept-5-en-2-onc dimethyl (5) and dibenzyl(6) acetals to give mixtures of regioisomeric triazolines. The latter gave the corresponding aziridines (6,6-dialkoxy-3-aza-8-oxatricyclo Introduction. ~ Recently, we proposed a total synthesis of D-and L-allose based on the double hydroxylation of the readily obtainable 7-oxabicyclo[2.2.l]hept-5-en-2-y1 derivatives 1 (derived from furan and (IS)-camphanic acid) and 2 (derived from furan and (1R)-camphanic acid), respectively [5]. E.g., 1 can be converted stereospecifically into ketone 3 which is then transformed via epoxidation of its (tert -butyl)dimethylsilyl enol ether into D-allose (4). Since 3-amino-3-deoxyhexoses are parts of many biologically active natural [6] [7] and unnatural products [8], we were interested in extending our approach to the stereoselective total synthesis of these important sugars. With this goal in mind, we have developed a method for the stereospecific amino-hydroxylation of the C(5)=C(6) bond in 7-oxabicyclo[2.2.l]hept-5-en-2-yl derivatives which allows us to report now the first total synthesis of derivatives of 3-amino-3-deoxyaltrose.

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Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 0^2,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives

Nativi

Reymond

Vogel

1989

Helvetica Chimica Acta

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A

Collins¹

1998

Dictionary of Carbohydrates

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M

Collins¹

1998

Dictionary of Carbohydrates

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The stereochemistry of palladium- and platinum-catalyzed hydrogenations of nitro sugar epoxides

Cited by 15 publications

References 47 publications

Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 0^2,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives

Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 0^2,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives

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The stereochemistry of palladium- and platinum-catalyzed hydrogenations of nitro sugar epoxides

Cited by 15 publications

References 47 publications

Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 02,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives

Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 02,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives

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Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 0^2,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives

Acid‐Catalyzed Rearrangement of 3‐Aza‐8‐oxatricyclo[3.2.1. 0^2,4]octan‐6‐one Acetals. Highly Stereoselective Total Synthesis of 3‐Amino‐3‐deoxy‐D‐altrose and Derivatives