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Two enantiomic natural products with wound-healing properties , alkannin ( 1 ) and shikonin ( 2 ), are accessible by a short and efficient total synthesis. The success was achieved by a novel protecting system for masking of 5,8-dihydroxy-1,4-naphthoquinones (naphthazarins) and a highly stereoselective ketone reduction. 相似文献
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New Asymmetric Synthesis of Alkannin and Shikonin 总被引:2,自引:0,他引:2
JianGangZHANC QunLU WenHuDUAN JunCaoCAI 《中国化学快报》2005,16(4):465-467
A new approach for asymmetric synthesis of alkannin and shikonin is presented. The chiral centers of the targets were introduced via an asymmetric C-arylation of-protected chiral glyceraldehyde in high de. The two enantiomers were prepared with the D-isopropylidenegly-ceraldehyde as the starting material. 相似文献
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Vassilios P. Papageorgiou Andreana N. Assimopoulou Elias A. Couladouros David Hepworth K. C. Nicolaou 《Angewandte Chemie (International ed. in English)》1999,38(3):270-301
Wound healing properties of plant extracts that contain the naphthoquinone natural products alkannin ( 1 ) and shikonin ( 2 ) have been known for many centuries. More recently, the biological properties of 1 , 2 , and related derivatives have been demonstrated experimentally, and their production both by cell cultures and chemical synthesis has been studied extensively. 相似文献
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Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin 下载免费PDF全文
Daler Baidilov Lukas Rycek John F. Trant Jordan Froese Brennan Murphy Tomas Hudlicky 《Angewandte Chemie (International ed. in English)》2018,57(34):10994-10998
Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps. 相似文献
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Based on the asymmetric reduction of alkannin ketone derivative 4 by diisopinocampheylchloro-borane(DIP-Cl), a series of shikonin and alkannin derivatives was designed, synthesized and their anticancer activities against various kinds of cell lines were evaluated. The in vitro biological experiments demonstrated that compound S-10, a 5,8-O-dimethyl-1,4-dioxime alkannin derivative, not only displayed excellent antiproliferative activity against cancer cells, but also exhibited low toxicity towards normal cells. It could induce HCT-116 cell apoptosis, but had no impact on the cell cycle. The underlying anticancer mechanism of S-10 is most likely different from other shikonin and alkannin derivatives. 相似文献
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Taku Shibue Toshihiro Hirai Dr. Iwao Okamoto Dr. Nobuyoshi Morita Dr. Hyuma Masu Prof. Dr. Isao Azumaya Prof. Dr. Osamu Tamura 《Chemistry (Weinheim an der Bergstrasse, Germany)》2010,16(38):11678-11688
The total syntheses of tetrapeptides tubulysins D ( 1 b ), U ( 1 c ), and V ( 1 d ), which are potent tubulin polymerization inhibitors, are described. The synthesis of Tuv ( 2 ), an unusual amino acid constituent of tubulysins, includes an 1,3‐dipolar cycloaddition reaction of chiral nitrone D ‐ 6 derived from D ‐gulose with N‐acryloyl camphor sultam (?)‐ 9 employing the double asymmetric induction, whereas the synthesis of Tup ( 20 ), another unusual amino acid, involves a stereoselective Evans aldol reaction of (Z)‐boron enolate generated from (S)‐4‐isopropyl‐3‐propionyl‐2‐oxazolidinone with N‐protected phenylalaninal and a subsequent Barton deoxygenation protocol. We accomplished the total syntheses of tubulysins U ( 1 c ) and V ( 1 d ) by using these methodologies, in which the isoxazolidine ring was used as the effective protective group for γ‐amido alcohol functionality. Furthermore, to understand the structure‐activity relationship of tubulysins, we synthesized tubulysin D ( 1 b ) and cyclo‐tubulysin D ( 1 e ) from 2 ‐Me and 20 , and ent‐tubulysin D (ent‐ 1 d ) from ent‐ 2 ‐Me and ent‐ 20 , respectively. The preliminary results regarding their biological activities are also reported. 相似文献
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A total synthesis of the vancomycin aglycon 1 has eluded synthetic chemists for so many years that the preparation of this molecule has become a vendetta for some groups. Finally, and almost simultaneously, research teams led by Evans and by Nicolaou have succeeded. Similarities and differences in their synthetic approaches are highlighted herein. 相似文献
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Georgy N. Varseev Dipl.‐Chem. Martin E. Maier Prof. Dr. 《Angewandte Chemie (International ed. in English)》2009,48(20):3685-3688
The right bicycle : A concise formal synthesis of platencin was based on an efficient oxygen‐mediated palladium‐catalyzed cycloalkenylation of 1 to form a bicyclo[3.2.1]octane, and a deoxygenative rearrangement of tosylhydrazone 2 to construct the bicyclo[2.2.2]octane 3 . The total yield of the core structure 4 of platencin was 17.5 % for 13 steps from a commercially available compound. Ts=p‐toluenesulfonyl, TBS=tert‐butyldimethylsilyl, Piv=pivaloyl.
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Byron K. Peters Jianguo Liu Cristiana Margarita Prof. Pher G. Andersson 《Chemistry (Weinheim an der Bergstrasse, Germany)》2015,21(19):7292-7296
The efficient and selective formal total synthesis of aliskiren is described. Aliskiren, a renin inhibitor drug, has received considerable attention, primarily because it is the first of the renin inhibitor drugs to be approved by the FDA. Herein, the formal synthesis of aliskiren by iridium‐catalyzed asymmetric hydrogenation of two allylic alcohol fragments is reported. Screening a number of N,P‐ligated iridium catalysts yielded two catalysts that gave the highest enantioselectivity in the hydrogenation, which gave the saturated alcohols in 97 and 93 % ee. In only four steps after hydrogenation, the fragments were combined by using the Julia–Kocienski reaction to produce late‐stage intermediate in an overall yield of 18 %. 相似文献
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A formal, total synthesis of aplysin has been described employing intermolecular (2+2) cycloaddition reaction between ketene and an olefin as a key step. 相似文献
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David A. Evans Michael R. Wood B. Wesley Trotter Timothy I. Richardson James C. Barrow Jeffrey L. Katz 《Angewandte Chemie (International ed. in English)》1998,37(19):2700-2704
Controlling the elements of planar and axial chirality are the principal challenges in the synthesis of the aglycon of vancomycin. Vancomycin is the prototypical member of the glycopeptide family of antibiotics which are effective for the treatment of infections by methicillin-resistant Staphylococcus aureus. The first total syntheses of the vancomycin and eremomycin aglycons provide insight into the influence of structure on kinetic and thermodynamic control of atropselective macrocyclizations. 相似文献
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Lisa Karmann Dr. Katharina Schultz Dr. Jennifer Herrmann Prof. Dr. Rolf Müller Prof. Dr. Uli Kazmaier 《Angewandte Chemie (International ed. in English)》2015,54(15):4502-4507
The miuraenamides, relatively simple representatives of a class of cyclodepsipeptides with high antitumor activity, can be easily and flexibly obtained by the concept of peptide modification. A reaction sequence consisting of an aldol reaction, oxidation, and methylation of the glycine subunit of the cyclodepsipeptides allows the incorporation of the unusual α,β‐unsaturated dehydroamino acid in one of the last steps of the synthesis. 相似文献