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Search for "corniculatolide" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities

Jorge de Lima Neto and
Paulo Henrique Menezes

Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31

called cyclic diaryl ether heptanoids (DAEH). This review is intended to highlight the structure elucidation, biosynthesis, and biological activity of these compounds as well as the use of different strategies for their synthesis. Keywords: combretastatin D; corniculatolide; isocorniculatolide

was used to isolate the known compound corniculatolide A (4, 10 mg) as colorless crystals [14]. Later the same group reported the isolation of corniculatolide B (9), isocorniculatolide B (10), and corniculatolide C (11) from Xylocarpus granatum, a tree commonly found in Southeast Asia and along the

hexane/acetone/MeOH to 20% MeOH. From the six main fractions, three of them showed the new structures, corniculatolide B (9, 3 mg), isocorniculatolide B (10, 2 mg), and corniculatolide C (11, 5 mg), among some other known constituents. Different 1H and 13C NMR and HRESIMS techniques were employed to

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Graphical Abstract

Figure 1: Structures of some members of the combretastatin D series, corniculatolides, and isocorniculatolide...

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Scheme 1: Biosynthetic pathway proposed by Pettit and co-workers.

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Scheme 2: Biosynthetic pathway towards corniculatolides or isocorniculatolides proposed by Ponnapalli and co-...

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Scheme 3: Retrosynthetic approaches.

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Scheme 4: Attempt of total synthesis of 2 by Boger and co-workers employing the Mitsunobu approach [27].

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Scheme 5: Total synthesis of combretastatin D-2 (2) reported by Boger and co-workers employing an intramolecu...

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Scheme 6: Formal synthesis of combretastatin D-2 (2) by Deshpande and co-workers using the Mitsunobu conditio...

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Scheme 7: Total synthesis of combretastatin D-2 (2) by Rychnovsky and Hwang [36].

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Scheme 8: Divergent synthesis of (±)-1 form combretastatin D-2 (2) by Rychnovsky and Hwang [36].

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Scheme 9: Enantioselective synthesis of 1 by Rychnovsky and Hwang employing Jacobsen catalyst [41].

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Scheme 10: Synthesis of fragment 57 by Couladouros and co-workers [43,45].

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Scheme 11: Formal synthesis of compound 2 by Couladouros and co-workers [43,45].

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Scheme 12: Synthesis of fragment 66 by Couladouros and co-workers [44,45].

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Scheme 13: Synthesis of fragment 70 by Couladouros and co-workers [44,45].

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Scheme 14: Synthesis of fragment 77 by Couladouros and co-workers [44,45].

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Scheme 15: Synthesis of combretastatins 1 and 2 by Couladouros and co-workers [44,45].

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Scheme 16: Formal synthesis of compound 2 by Gangakhedkar and co-workers [48].

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Scheme 17: Synthesis of fragment 14 by Cousin and co-workers [50].

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Scheme 18: Synthesis of fragment 91 by Cousin and co-workers [50].

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Scheme 19: Formal synthesis of compound 2 by Cousin and co-workers [50].

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Scheme 20: Synthesis of 2 diolide by Cousin and co-workers [50].

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Scheme 21: Synthesis of combretastatin D-4 (4) by Nishiyama and co-workers [54].

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Scheme 22: Synthesis of fragment 112 by Pettit and co-workers [55].

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Scheme 23: Synthesis of fragment 114 by Pettit and co-workers [55].

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Scheme 24: Attempt to the synthesis of compound 2 by Pettit and co-workers [55].

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Scheme 25: Synthesis of combretastatin-D2 (2) starting from isovanilin (80) by Pettit and co-workers [55].

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Scheme 26: Attempted synthesis of combretastatin-D2 (2) derivatives through an S_NAr approach [55].

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Scheme 27: Synthesis of combretastatin D-4 (4) by Pettit and co-workers [55].

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Scheme 28: Synthesis of combretastatin D-2 (2) by Harras and co-workers [57].

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Scheme 29: Synthesis of combretastatin D-4 (4) by Harras and co-workers [57].

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Scheme 30: Formal synthesis of combretastatin D-1 (1) by Harras and co-workers [57].

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Scheme 31: Synthesis of 11-O-methylcorniculatolide A (5) by Raut and co-workers [69].

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Scheme 32: Synthesis of isocorniculatolide A (7) and O-methylated isocorniculatolide A 8 by Raut and co-worker...

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Scheme 33: Synthesis of isocorniculatolide B (10) and hydroxyisocorniculatolide B 175 by Kim and co-workers [71].

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Scheme 34: Synthesis of compound 9, 178, and 11 by Kim and co-workers [71].

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Scheme 35: Synthesis of combretastatin D-2 prodrug salts [55].

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Figure 2: ED₅₀ values of the combretastatin D family against murine P388 lymphocytic leukemia cell line (appr...

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Figure 3: IC₅₀ of compounds against α-glucosidase [19].

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Review

Published 29 Mar 2023

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