- Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
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The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B and C.
- Shimada, Naoyuki,Takahashi, Naoya,Ohse, Naoki,Koshizuka, Masayoshi,Makino, Kazuishi
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supporting information
p. 13145 - 13148
(2020/11/09)
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- Concise access toward chiral hydroxy phenylpropanoids: formal synthesis of virolongin B; kigelin; kurasoin A; 4-hydroxysattabacin, and actinopolymorphol A
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A simple, two step strategy consisting of Sharpless asymmetric dihydroxylation followed by regioselective breaking of [Formula presented] bond is utilized to target key chiral intermediates of natural products virolongin B, kigelin, kurasoin A, 4-hydroxy-sattabacin, and actinopolymorphol A. Derivatives of enantiopure hydroxy phenyl propanoids and α-hydroxy Weinreb amides are synthesized. The reductive cleavage of [Formula presented] bond in a regioselective manner is obtained using Pd/C in methanol.
- Patil, Sagar N.,Tilve, Santosh G.
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supporting information
p. 3371 - 3375
(2016/07/11)
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- Concise, protecting group free total syntheses of (+)-sattabacin and (+)-4-hydroxysattabacin
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The first asymmetric total syntheses of the antiviral natural products (+)-sattabacin and (+)-4-hydroxysattabacin are reported. Both total syntheses are remarkably concise and were completed without the use of protecting groups. These syntheses allowed the unambiguous assignment of the absolute configuration of both natural products. The syntheses of these natural products, which exhibit marked antiviral activity, are readily amenable to the preparation of structural analogs and progress in this regard is also reported.
- Aronoff, Matthew R.,Bourjaily, Neil A.,Miller, Kenneth A.
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supporting information; experimental part
p. 6375 - 6377
(2011/01/03)
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- Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation
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The total synthesis of the farnesyltransferase inhibitor kurasoin A has been achieved using a novel asymmetric phase-transfer-catalyzed glycolate alkylation reaction. 2,5-Dimethoxyacetophenone 7 with cinchonidinium catalyst 9 (10 mol %) and hydroxide base
- Andrus, Merritt B.,Hicken, Erik J.,Stephens, Jeffrey C.,Bedke, D. Karl
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p. 8651 - 8654
(2007/10/03)
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