Synthesis of 24a-Substituted Milbemycin A<sub>4</sub> Derivatives and Their Acaricidal Activity against <i>Tetranychus uvticae</i>

Tsukamoto, Yoshihisa; Kajino, Hisaki; Sato, K.; Tanaka, Keiji; Yanai, Toshiaki

doi:10.1271/bbb.61.806

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“…Naturally occurring spiroketals exhibit a wide spectrum of biological activity: anticancer [ 20 – 22 ], antibiotic [ 23 – 24 ], antifungal [ 25 ], anthelmintic [ 26 ] and anti-HIV [ 27 ]. A previously mentioned example of a protein phosphatase inhibitor okadaic acid is a toxin associated with diarrheic shellfish poisoning [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Čikoš

Ćaleta

Žiher

et al. 2015

Beilstein J. Org. Chem.

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SummaryThree novel spiroketals were prepared by a one-pot transformation of 6-O-methyl-9(E)-hydroxyiminoerythronolide A. We present the formation of a [4.5]spiroketal moiety within the macrolide lactone ring, but also the unexpected formation of a 10-C=11-C double bond and spontaneous change of stereochemistry at position 8-C. As a result, a thermodynamically stable structure was obtained. The structures of two new diastereomeric, unsaturated spiroketals, their configurations and conformations, were determined by means of NMR spectroscopy and molecular modelling. The reaction kinetics and mechanistic aspects of this transformation are discussed. These rearrangements provide a facile synthesis of novel macrolide scaffolds.

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Section: Introductionmentioning

confidence: 99%

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Čikoš

Ćaleta

Žiher

et al. 2015

Beilstein J. Org. Chem.

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Isolation and identification of three new isomer impurities in milbemycin oxime drug substance

Ren,

Lu,

et al. 2024

J Antibiot

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Synthesis of 24a-Substituted Milbemycin A₄ Derivatives and Their Acaricidal Activity against Tetranychus uvticae

Cited by 2 publications

References 2 publications

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Isolation and identification of three new isomer impurities in milbemycin oxime drug substance

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Synthesis of 24a-Substituted Milbemycin A4 Derivatives and Their Acaricidal Activity against Tetranychus uvticae

Cited by 2 publications

References 2 publications

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A

Isolation and identification of three new isomer impurities in milbemycin oxime drug substance

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Product

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Synthesis of 24a-Substituted Milbemycin A₄ Derivatives and Their Acaricidal Activity against Tetranychus uvticae