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Literature DB >> 28252949

Stereocontrolled Synthesis of Kalihinol C.

Abstract

We report a concise chemical synthesis of kalihinol C via a possible biosynthetic intermediate, "protokalihinol", which was targeted as a scaffold en route to antiplasmodial analogs. High stereocontrol of the kalihinol framework relies on a heterodendralene cascade to establish the target stereotetrad. Common problems of regio- and chemoselectivity encountered in the kalihinol class are explained and solved.

Entities: Chemical Disease Mutation Species

Mesh：

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Year: 2017 PMID： 28252949 PMCID： PMC5854479 DOI： 10.1021/jacs.7b01124

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

21 in total

1. Antiplasmodial activity: the first proof of inhibition of heme crystallization by marine isonitriles.

Authors: Ryan M Young; Matthew R Adendorff; Anthony D Wright; Michael T Davies-Coleman
Journal: Eur J Med Chem Date: 2015-02-09 Impact factor: 6.514

2. Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines.

Authors: Sergey V Pronin; Christopher A Reiher; Ryan A Shenvi
Journal: Nature Date: 2013-09-12 Impact factor: 49.962

3. Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.

Authors: Hai-Hua Lu; Sergey V Pronin; Yevgeniya Antonova-Koch; Stephan Meister; Elizabeth A Winzeler; Ryan A Shenvi
Journal: J Am Chem Soc Date: 2016-05-31 Impact factor: 15.419

4. Total synthesis of antimalarial diterpenoid (+)-kalihinol A.

Authors: Hiroaki Miyaoka; Yasunori Abe; Nobuaki Sekiya; Hidemichi Mitome; Etsuko Kawashima
Journal: Chem Commun (Camb) Date: 2011-12-05 Impact factor: 6.222

5. Juxtaposition of chemical and mutation-induced developmental defects in zebrafish reveal a copper-chelating activity for kalihinol F.

Authors: Imelda T Sandoval; Elizabeth J Manos; Ryan M Van Wagoner; Richard Glenn C Delacruz; Kornelia Edes; Dennis R Winge; Chris M Ireland; David A Jones
Journal: Chem Biol Date: 2013-06-20

3. Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents.

Authors: Raphael K Klake; Samantha L Gargaro; Skyler L Gentry; Sharon O Elele; Joshua D Sieber
Journal: Org Lett Date: 2019-09-18 Impact factor: 6.005

3 in total

Stereocontrolled Synthesis of Kalihinol C.

1. Antiplasmodial activity: the first proof of inhibition of heme crystallization by marine isonitriles.

2. Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines.

3. Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.

4. Total synthesis of antimalarial diterpenoid (+)-kalihinol A.

5. Juxtaposition of chemical and mutation-induced developmental defects in zebrafish reveal a copper-chelating activity for kalihinol F.

6. Dendralenes branch out: cross-conjugated oligoenes allow the rapid generation of molecular complexity.

Review 7. Syntheses and biological studies of marine terpenoids derived from inorganic cyanide.

8. Pseudopterosin synthesis from a chiral cross-conjugated hydrocarbon through a series of cycloadditions.

9. Synthesis and potent antimalarial activity of kalihinol B.

10. Antimalarial Properties of Simplified Kalihinol Analogues.

1. The High Chemofidelity of Metal-Catalyzed Hydrogen Atom Transfer.

2. Diverse secondary C(sp³)-H bond functionalization via site-selective trifluoroacetoxylation of aliphatic amines.

3. Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents.