- Microwave-mediated nickel-catalyzed cyclotrimerization reactions: Total synthesis of illudinine
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(Chemical Equation Presented) Rapid and efficient [2 + 2 + 2] cyclotrimerization reactions were discovered through the application of microwave irradiation in conjunction with a Ni(CO)2(PPh 3)2 catalyst. This enables the f
- Teske, Jesse A.,Deiters, Alexander
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- Synthesis of Illudinine from Dimedone and Identification of Activity as a Monoamine Oxidase Inhibitor
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The fungal metabolite illudinine is prepared in seven steps and ca. 55% overall yield from dimedone using an open and shut (ring-opening and ring-closing) strategy. Tandem ring-opening fragmentation and olefination of dimedone establishes alkyne and vinylarene functionality linked by a neopentylene tether. Oxidative cycloisomerization then provides the illudinine framework. The key innovation in this second-generation synthesis of illudinine is the use of the nitrile functional group, rather than an ester, as the functional precursor to the carboxylic acid of illudinine. The small, linear nitrile (CN) is associated with improved selectivity, π-conjugation, and reactivity at multiple points in the synthetic sequence relative to the carboxylic acid ester. Preliminary assays indicate that illudinine and several related synthetic analogues are monoamine oxidase inhibitors, which is the first reported indication of biological activity associated with this natural product. Illudinine was found to inhibit monoamine oxidase B (MAO-B) with an IC50of 18 ± 7.1 μM in preliminary assays.
- Gaston, Robert,Geldenhuys, Werner J.,Dudley, Gregory B.
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p. 13429 - 13437
(2020/12/15)
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- Synthesis of Illudinine from Dimedone
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A total synthesis of the illudalane sesquiterpene illudinine was realized in eight steps and 14% overall yield from commercially available dimedone. The approach features tandem fragmentation/Knoevenagel-type condensation and microwave-assisted oxidative
- Morrison, Alec E.,Hoang, Tung T.,Birepinte, Mélodie,Dudley, Gregory B.
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p. 858 - 861
(2017/02/26)
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- Synthesis of isoquinolines from indanones: Total synthesis of illudinine
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Schmidt reaction of 5-methoxy or 7-methoxyindan-1-ones or their derivatives results exclusively in isocarbostyrils which are converted into 6-methoxy or 8-methoxyisoquinolines in good yields.This strategy has been extended to the total synthesis of illudinine methyl ester (1b) starting from methyl 8-methoxy-2,2-dimethyl-7-oxo-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate (4).
- Shanker, P. Sathya,Rao, G. S. R. Subba
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p. 1209 - 1213
(2007/10/02)
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