Regioselective oxidation of terfenadine with Cunninghamella blakesleeana

: A new synthesis of the 2,6-naphthyridine alkaloid 4-methyl-2,6-naphthyridine from Antirrhinum majus has been developed. Key steps are a regioselective oxidation of 3-bromo-4,5- dimethylpyridine to the corresponding 4-formyl derivative, and the annulation of the second pyridine ring by Suzuki-Miyaura cross-coupling using (E)-2-ethoxyvinylboronic acid pinacol ester as a masked acetaldehyde equivalent. This protocol gives the alkaloid in four steps starting from commercially available 3,4-dimethylpyridine in 15% overall yield. This annulation protocol should be useful for the synthesis of other condensed pyridines as well.

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ChemInform Abstract: SYNTHETIC METHODS AND REACTIONS. 35. REGIOSELECTIVE OXIDATION OF ALKYL (CYCLOALKYL) METHYL ETHERS TO CARBONYL COMPOUNDS WITH NITRONIUM TETRAFLUOROBORATE

Chemischer Informationsdienst ◽

10.1002/chin.197801132 ◽

1978 ◽

Vol 9 (1) ◽

Author(s):

T. L. HO ◽

G. A. OLAH

Keyword(s):

Carbonyl Compounds ◽

Synthetic Methods ◽

Regioselective Oxidation ◽

Nitronium Tetrafluoroborate

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Catalytic and Regioselective Oxidation of Carbohydrates To Synthesize Keto-Sugars under Mild Conditions

Organic Letters ◽

10.1021/ol502344h ◽

2014 ◽

Vol 16 (18) ◽

pp. 4846-4849 ◽

Cited By ~ 19

Author(s):

Wataru Muramatsu

Keyword(s):

Mild Conditions ◽

Regioselective Oxidation

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Regioselective oxidation of 2-amino-3-aroyl-4,5-dialkylthiophenes by DMSO

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2003.12.010 ◽

2004 ◽

Vol 14 (4) ◽

pp. 929-933 ◽

Cited By ~ 5

Author(s):

Elizabeth Joshi ◽

Mahendra D. Chordia ◽

Timothy L. Macdonald ◽

Joel Linden ◽

Ray Olsson

Keyword(s):

Regioselective Oxidation

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ChemInform Abstract: MICROBIAL TRANSFORMATION OF (-)-Δ1-3,4-TRANS-TETRAHYDROCANNABINOL BY CUNNINGHAMELLA BLAKESLEEANA LENDER

Chemischer Informationsdienst ◽

10.1002/chin.197641364 ◽

1976 ◽

Vol 7 (41) ◽

pp. no-no

Author(s):

MICHAEL BINDER

Keyword(s):

Microbial Transformation ◽

Cunninghamella Blakesleeana

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A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine

The Journal of Organic Chemistry ◽

10.1021/jo00120a016 ◽

1995 ◽

Vol 60 (15) ◽

pp. 4743-4748 ◽

Cited By ~ 86

Author(s):

Stefano Cicchi ◽

Andrea Goti ◽

Alberto Brandi

Keyword(s):

Malic Acid ◽

Regioselective Oxidation

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Critical Review of Biotransformational Studies on Steroids by Using Culture of Cunninghamella blakesleeana

Letters in Organic Chemistry ◽

10.2174/1570178618666210820110400 ◽

2021 ◽

Vol 18 ◽

Author(s):

Azizuddin ◽

Muhammad Iqbal ◽

Syed Ghulam Musharraf

Keyword(s):

Double Bond ◽

Critical Review ◽

Structural Modification ◽

Bond Formation ◽

Environmentally Friendly ◽

Side Chain ◽

Synthetic Compounds ◽

Efficient Approach ◽

Cunninghamella Blakesleeana ◽

Different Strains

: For several decades, biotransformational studies on steroidal compounds have gained a lot of attention because it is an efficient approach for the structural modification of complicated natural or synthetic compounds with high regio-, chemo- and stereoselectivity at environmentally friendly conditions. This review summarizes the use of different strains of Cunninghamella blakesleeana for the biotransformation of sixteen steroids 1-16 into a variety of transformed products. The transformed products may be important as a drug or precursor for the production of important pharmaceuticals. The types of reactions performed by C. blakesleeana include hydroxylation, epoxidation, reduction, demethylation, oxidation, glycosidation, double bond formation, side-chain degradation, isomerisation and opening of an isoxazol ring, which would be difficult to produce by traditional synthesis.

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