A Partial Synthesis of 23-Hydroxybetulonic Acid and 23-Hydroxybetulinic Acid Starting from Betulinic Acid

Sun, Fei; Zhu, Peiqing; Yao, Hequan; Wu, Xiaoming; Xu, Jinyi

doi:10.3184/174751912x13332875186150

Cited by 10 publications

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References 15 publications

(11 reference statements)

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“…5 has been previously synthesized from betulinic acid using a Baldwin-type C–H oxidation. [21] In that study, transformation of the alcohol into an oxime directing group, C–H oxidation with stoichiometric palladium and then two-step regeneration of the alcohol was required. Hartwig’s conditions avoided these four steps of functional group manipulations and do not necessitate protection of the C20–C21 alkene.…”

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Improving Physical Properties via CH Oxidation: Chemical and Enzymatic Approaches

et al. 2014

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Physicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycle-type leads exist, complex hydrocarbon skeletons are more challenging to derivatize due to the absence of functional groups. A variety of C–H oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly water soluble, natural product. Capitalizing on the innate reactivity of the molecule, as well as the few molecular handles present on the core, allowed for oxidations at different positions across the pentacyclic structure. Enzymatic oxidations afforded several orthogonal oxidations to chemical methods. Solubility measurements showed an enhancement for many of the synthesized compounds.

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confidence: 99%

Improving Physical Properties via CH Oxidation: Chemical and Enzymatic Approaches

et al. 2014

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“…A two‐step debenzylation delivered the natural product C23‐hydroxybetulinic acid ( 5 ). Compound 5 has been previously synthesized from betulinic acid using a Baldwin‐type CH oxidation 21. In that study, transformation of the alcohol into an oxime directing group, CH oxidation with stoichiometric palladium, and then two‐step regeneration of the alcohol was required.…”

Section: Relative Solubility Enhancement Of the Oxidized Compoundsmentioning

confidence: 99%

Improving Physical Properties via CH Oxidation: Chemical and Enzymatic Approaches

et al. 2014

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Physicochemical properties constitute a key factor for the success of a drug candidate. Whereas many strategies to improve the physicochemical properties of small heterocycletype leads exist, complex hydrocarbon skeletons are more challenging to derivatize because of the absence of functional groups. A variety of C À H oxidation methods have been explored on the betulin skeleton to improve the solubility of this very bioactive, yet poorly water-soluble, natural product. Capitalizing on the innate reactivity of the molecule, as well as the few molecular handles present on the core, allowed oxidations at different positions across the pentacyclic structure. Enzymatic oxidations afforded several orthogonal oxidations to chemical methods. Solubility measurements showed an enhancement for many of the synthesized compounds.

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ChemInform Abstract: A Partial Synthesis of 23‐Hydroxybetulonic Acid and 23‐Hydroxybetulinic Acid Starting from Betulinic Acid.

et al. 2012

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A Partial Synthesis of 23-Hydroxybetulonic Acid and 23-Hydroxybetulinic Acid Starting from Betulinic Acid. -Betulinic acid (I) is used in the traditional Chinese medicine for the treatment of amoebic dysentery and malaria. Betulinic acid is easily obtained from the bark of varios trees. The target compounds (VI) and (VII) exhibit anti-tumor and anti-HIV activities. -(SUN, F.; ZHU, P.; YAO, H.; WU, X.; XU*, J.; J. Chem. Res. 36 (2012) 5, 254-257,

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A Partial Synthesis of 23-Hydroxybetulonic Acid and 23-Hydroxybetulinic Acid Starting from Betulinic Acid

Cited by 10 publications

References 15 publications

Improving Physical Properties via CH Oxidation: Chemical and Enzymatic Approaches

Improving Physical Properties via CH Oxidation: Chemical and Enzymatic Approaches

Improving Physical Properties via CH Oxidation: Chemical and Enzymatic Approaches

ChemInform Abstract: A Partial Synthesis of 23‐Hydroxybetulonic Acid and 23‐Hydroxybetulinic Acid Starting from Betulinic Acid.

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