Synthesis of (.+-.)-fredericamycin A

Kelly, T. Ross; Bell, Stephen H.; Ohashi, Naohito; Armstrong-Chong, Rosemary J.

doi:10.1021/ja00227a030

Cited by 111 publications

(61 citation statements)

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“…Most recent synthetic efforts have focused on stereoselective cyclopropanation reactions. [3] On the other hand, the syntheses of many 2-pyridinecontaining compounds [4] have been developed because these moieties are contained in potent antitumor, [5] antiviral [6] and antimicrobial [7] agents. We envisioned that 2-pyridones fused with cyclopropane rings might present interesting biological activities or be useful intermediates in syntheses of bioactive products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Azabicyclo[4.1.0]heptanes through Stereoselective Cyclopropanation Reactions

Villar¹,

Gradillas²,

Pérez‐Castells³

2010

Eur J Org Chem

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Unsaturated δ‐lactams are cyclopropanated with the aid of diazo compound decomposition catalysed by metal complexes. A study of the reaction conditions, stereochemical outcome and group protection is reported. The resulting bicyclic products are related to bioactive compounds. Transformation into thiolactams facilitates the separation of the different isomers obtained and the removal of the protecting group. The cyclopropanation reaction works with diverse diazo compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2‐Azabicyclo[4.1.0]heptanes through Stereoselective Cyclopropanation Reactions

Villar¹,

Gradillas²,

Pérez‐Castells³

2010

Eur J Org Chem

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“…Dienediolates, prepared from unsaturated carboxylic acids, often lead to pyridones in high yield, especially when R 6 is a non enolizable group [124][125][126]. With enolates prepared from primary and secondary amides, the reactive species would be a dianion with, presumably, an enhanced nucleophilicity [127]. A reasonable speculation is that this problem is due to deprotonation of the nitrile by the nucleophile, followed by self-condensation.…”

Section: From C 4 + C 1 Building Blocksmentioning

confidence: 99%

“…Fredericamycin A has been established as an important new lead compound for the chemotherapy of human cancers [28,29]. Fredericamycin A has been established as an important new lead compound for the chemotherapy of human cancers [28,29].…”

Section: Introductionmentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

198

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The synthesis of a substituted 2-pyridone ring is a topical area of continuing interest due to the number of biologically active molecules containing this moiety. Over the last decade, natural compounds with this structure have emerged as potent antitumor antiviral and attention, because those compounds may be studied as a simple model for investigating mechanisms of some enzymatic reactions or for discerning the behavior of nucleic acids bases in connection with mutation due to base mispairing or other mistaken helices. Recent studies have shown the usefulness of 2-pyridones as intermolecular connectors between building blocks in material science. Thus, despite the large number of methods known for their synthesis, new procedures are continuously being developed. Two main synthetic approaches can be found in the literature: from other heterocycles systems or condensation of acyclic systems. The latter can be further classified depending on the bond formed in the cyclization step: by C-C or C-N bond generation. The latter can be subclassified depending on the first condensation step. This is a review of new or improved methods for constructing 2-pyridone rings. This article will be restricted to ring formation, which can be included in the total synthesis of several compounds with specific biological or material properties.The pursuit of these properties requires efficient synthetic routes that allow rapid assembly and variation of multiple pendant substituents on the heteroaromatic case, which permits rapid analogsynthesis (RAS) [1].

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“…Reactions of aryl amide enolates with nitriles to afford 2-isoquinolines are known, 7 but our studies on the reactivity of dienediolates from unsaturated carboxylic acids had led us to a simpler synthesis of 4,6-disubstituted-and 3,4,6-trisubstituted-2-pyridones from easily accessible carboxylic acids and nitriles. 8 On work-up, pure pyridone was isolated from the neutral fraction whereas the starting acid was recovered from the acidic fraction.…”

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confidence: 99%