General entries to C-aryl glycosides. Formal synthesis of galtamycinone

Apsel, Beth; Bender, John A.; Escobar, Maya; Kaelin, David E.; López, Omar D.; Martin, Stephen F.

doi:10.1016/s0040-4039(02)02666-7

Cited by 43 publications

(36 citation statements)

References 15 publications

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“…21 This important family of compounds has long attracted interest because of their broad range of biological activities and their resistance to enzymatic hydrolysis. Some C -aryl glycosides that were of interest included galtamycinone 22 and vineomycinone B 2 methyl ester, 23 two representative members of the Group II C -aryl glycosides, 5-hydroxyaloin A, 24 a Group I C -aryl glycoside, as well as kidamycin and its isomer isokidamycin, 25 which belong to the Group III C -aryl glycoside family (Figure 3 ) .…”

Section: Furans As Building Blocks For C-aryl Glycoside Synthesismentioning

confidence: 99%

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Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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Diverse structural types of natural products and their mimics have served as targets of opportunity in our laboratory to inspire the discovery and development of new methods and strategies to assemble polyfunctional and polycyclic molecular architectures. Furthermore, our efforts toward identifying novel compounds having useful biological properties led to the creation of new targets, many of which posed synthetic challenges that required the invention of new methodology. In this Perspective, selected examples of how we have exploited a diverse range of natural products and their mimics to create, explore, and solve a variety of problems in chemistry and biology will be discussed. The journey was not without its twists and turns, but the unexpected often led to new revelations and insights. Indeed, in our recent excursion into applications of synthetic organic chemistry to neuroscience, avoiding the more-traveled paths was richly rewarding.

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Section: Furans As Building Blocks For C-aryl Glycoside Synthesismentioning

confidence: 99%

“…22 Introduction of the silyl tethering group onto the furan ring of 75 was easily achieved by regioselective metalation, followed by appending a functionalized silyl side chain to furnish 77 .…”

Section: Furans As Building Blocks For C-aryl Glycoside Synthesismentioning

confidence: 99%

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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“…In a two-step process, the nucleophilic addition to lactone by an organometallic reagent followed by reduction of the resulting lactol, provided the aryl C-glycosides in better yields. For example, galtamycinone was synthesized from lactone 57 as shown in Scheme 10 [35]. …”

Section: Lactonesmentioning

confidence: 99%

“…An alternative method was to form the aromatic ring after the Pd-catalyzed S N 2' ring opening-oxidation (Scheme 20). Martin and co-workers successfully applied this protocol to the synthesis of galtamycinone [35]. The dihydronaphthol 94 obtained by a palladium-mediated cross-coupling was oxidized by DDQ to yield aryl C-glycoside 95.…”

Section: Cross-couplingmentioning

confidence: 99%

“…DielsAlder reaction is one of the most powerful reactions to build six-membered rings, including aromatic rings. Martin and co-workers have developed an efficient cycloaddition protocol using 2-glycosyl furan 101 as dienes (Scheme 22) [35,51]. The glycosyl furan obtained from sugar lactone reacted with the benzyne derivatives generated in situ to Scheme (18).…”

Section: Cyclizationsmentioning

confidence: 99%

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Recent Advances in Aryl C-Glycoside Synthesis

Lee

He²

2005

CTMC

104

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Aryl C-glycosides are stable analogs of the corresponding O-glycosides. Because of their favorable pharmacological profiles attributed primarily to the C-glycosyl moiety, aryl C-glycosides have gained increasing popularity as drug candidates. In this review we focus on the synthesis of aryl C-glycosides including puerarin and kendomycin. This review is organized based on the type of chemistry used in the assembly of the C-glycosides with the following sub-sections: electrophilic reaction, cross-coupling reaction, free radical reaction, cyclization, intramolecular O-C rearrangement, umpolung, and miscellaneous reactions.

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Arylation Reactions Involving the Formation of Arynes

Chen

Larock

2009

Modern Arylation Methods

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General entries to C-aryl glycosides. Formal synthesis of galtamycinone

Cited by 43 publications

References 15 publications

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Recent Advances in Aryl C-Glycoside Synthesis

Arylation Reactions Involving the Formation of Arynes

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