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  • Title: Divergent synthesis and evaluation of inhibitory activities against cyclooxygenases-1 and -2 of natural withasomnines and analogues.
    Author: Usami Y, Watanabe R, Fujino Y, Shibano M, Ishida C, Yoneyama H, Harusawa S, Ichikawa H.
    Journal: Chem Pharm Bull (Tokyo); 2012; 60(12):1550-60. PubMed ID: 23207635.
    Abstract:
    The divergent synthesis of natural withasomnines and analogues was achieved from 4-hydroxypyrazoles, which was prepared via alkaline hydrolysis of the Baeyer-Villiger oxidation products from 4-formylpyrazoles. Key steps of this synthesis are regioselective Claisen rearrangement of 4-allyloxypyrazoles and the Suzuki-Miyaura coupling of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl trifluoromethanesulfonate and commercially available arylboronic acids. The Suzuki-Miyaura coupling at the final step of this strategy enabled facile access to natural withasomnines and their analogues. The biological activities of the twelve synthesized compounds against cyclooxygenases-1 and -2 (COX-1 and COX-2) were evaluated.
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