Synthesis of actinomycin analogs: XXIV. Non-symmetric derivatives of actinocin containing benzo-18-crown-6 moiety and tertiary ammonium group

Ovchinnikov, D. V.; Ponyaev, A. I.

doi:10.1134/s1070363216120070

Cited by 1 publication

(1 citation statement)

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“…The development of methodology which allows selective oxidation of one specific aminophenol partner and controlled coupling with a second unit has not been achieved yet. Strong oxidizing reagents are often used which lead to oxidation of both reactants and reduces the overall efficiency. − To overcome these drawbacks, we sought to achieve a selective cross-coupling through use of an electron rich aminophenol component in combination with a mild and eco-friendly oxidant which does not affect the less electron rich 2-aminophenol coupling partner.…”

Section: Introductionmentioning

confidence: 99%

Xylochemical Synthesis of Cytotoxic 2-Aminophenoxazinone-Type Natural Products Through Oxidative Cross Coupling

Kühlborn

Konhäuser

Groß

et al. 2019

ACS Sustainable Chem. Eng.

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Today, the total synthesis of natural products mostly relies on the use of petroleum-based starting materials. The commercial availability of building blocks of this type often deflects attention away from lengthy synthetic routes required for the reintroduction of heteroatom substitution patterns lost in the geological process of kerogenesis. Herein, the use of wood-based starting materials, the so-called xylochemicals, for the synthesis of 2-aminophenoxazinone natural products is presented. The inherent heteroatom substitution patterns as well as chemical functionalities were employed and permitted a short and straightforward synthetic strategy. Moreover, a novel and “green” method for constructing the 2-aminophenoxazinone moiety was developed. A series of natural products was prepared and their cytotoxic properties were examined.

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