Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products

Fraser‐Reid, Bert; Anderson, Robert C.

doi:10.1007/978-3-7091-8551-3_1

Cited by 48 publications

(5 citation statements)

References 95 publications

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“…Alkaline hydrolysis yielded guanidine and the carboxylic acid (547). It was therefore presumed that the (546) The stereochemistry of the double bonds was assigned as E by the synthesis of triophamine (546) outlined in Scheme 40 (709).…”

Section: O~nh _~ N~mentioning

confidence: 99%

“…Many approaches have been developed for the synthesis of enantiomerically pure tetrodotoxin among them KEANA'S (532-538), IsOBE'S (539-541) and other approaches(543)(544)(545)(546)(547)(548). Many approaches have been developed for the synthesis of enantiomerically pure tetrodotoxin among them KEANA'S (532-538), IsOBE'S (539-541) and other approaches(543)(544)(545)(546)(547)(548).…”

mentioning

confidence: 99%

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Some Aspects of Guanidine Secondary Metabolites

Berlinck

1995

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Section: O~nh _~ N~mentioning

confidence: 99%

mentioning

confidence: 99%

Some Aspects of Guanidine Secondary Metabolites

Berlinck

1995

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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“…Highly functionalized acyclic monosaccharide derivatives are products of interest in organic synthesis with utility as building blocks for the synthesis of bioactive compounds . The elongation of the monosaccharide chain with the incorporation of an epoxide group is especially interesting, taking into account the diverse synthetic possibilities that this functional group offers .…”

Section: Introductionmentioning

confidence: 99%

Reaction of O-Benzyl- and 4,6-O-Benzylidene-d-Gluco- and d-Galactopyranose Derivatives with Amide-Stabilized Sulfur Ylides: Stereoselectivity and Reactivity

et al. 1998

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The reaction of N,N-diethyl-2-(dimethylsulfuranylidene)acetamide (1) with protected monosaccharides has been extended to several O-benzyl- and 4,6-O-Benzylidene-d-gluco- and -d-galactopyranose derivatives. When the monosaccharide is 2,3,4,6-tetra-O-benzyl-d-glucose (6) or d-galactose (9), elimination of the 3-benzyloxy substituent occurs, to give the unsaturated epoxyamides 7 and 10, respectively, in reasonable yields and poor stereoselectivity. On the other hand, the reaction of 1 with the 4,6-O-benzylidene-d-glucopyranose derivatives 11, 14, and 17 yielded the corresponding epoxyamides 12, 15a:15b, and 18a:18b in good yields and variable stereoselectivity. In accordance with previous studies concerning the configurational assignments for the epoxide derivatives 3, 5a, and 21, obtained from 2, 4, and 20, respectively, the present article confirms the role of the hydroxyl group at C-2 on the stereselectivity of the reaction. Thus, when the C-2 OH is unprotected (4, 11, 20), the major epoxide formed has the configuration 2S, 3R (epoxyamides 5a, 12, and 21). Conversely, derivatives with the hydroxyl group protected at C-2, or 2-deoxy sugars (2, 14, and 17), yield as the major epoxides the corresponding 2R, 3S isomers (3, 15b, and 18b).

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“…Convergent, bottom-up approaches to these targets require enantio- and diastereoselective reactions to forge the stereochemical information, a property already inherent to carbohydrates. Top-down methodologies from sustainable and cheap cellulosic starting materials date back decades , but are undergoing a resurgence …”

mentioning

confidence: 99%

Borane- and Silylium-Catalyzed Difunctionalization of Carbohydrates: 3,6-Anhydrosugar Enabled 1,6-Site Selectivity

et al. 2022

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A novel diastereoselective, Lewis acid catalyzed 1,6-difunctionalization of galactose and mannose derivatives has been developed in one pot, via sequential nucleophile additions. Our studies point to the formation of a 3,6-anhydrosugar intermediate as key to the 1,6-site-selectivity. Starting material-specific reactivity occurs when competitive ring-opening C–O cleavage is possible, owed to basicity and stereoelectronic stabilization differences. Lastly, Mayr nucleophilicity parameter values helped predict which reaction conditions would be most suitable for specific nucleophiles.

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Carbohydrate Derivatives in the Asymmetric Synthesis of Natural Products

Cited by 48 publications

References 95 publications

Some Aspects of Guanidine Secondary Metabolites

Some Aspects of Guanidine Secondary Metabolites

Reaction of O-Benzyl- and 4,6-O-Benzylidene-d-Gluco- and d-Galactopyranose Derivatives with Amide-Stabilized Sulfur Ylides: Stereoselectivity and Reactivity

Borane- and Silylium-Catalyzed Difunctionalization of Carbohydrates: 3,6-Anhydrosugar Enabled 1,6-Site Selectivity

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