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Tuesday, May 19, 2020 | History

2 edition of Approaches towards a total synthesis of rhizoxin. found in the catalog.

Approaches towards a total synthesis of rhizoxin.

Richard John Davenport

Approaches towards a total synthesis of rhizoxin.

by Richard John Davenport

  • 37 Want to read
  • 21 Currently reading

Published by University of Manchester in Manchester .
Written in English


Edition Notes

Manchester thesis (M.Sc.), Department of Chemistry.

ContributionsUniversity of Manchester. Department of Chemistry.
The Physical Object
Pagination88p.
Number of Pages88
ID Numbers
Open LibraryOL16572706M

Section four describes modern approaches for controlling regioselectivity in carbohydrate synthesis. The final section focuses on new developments in the construction of "unusual" sugars and is rounded off by a presentation of modern procedures for the construction of glycosylated natural products. Marc Liniger (): Total Synthesis and Biological Evaluation of Antitumor Natural Products and their Analogs: Rhizoxin WFF and 4'-Deoxy-L Raphael Schiess (): Total Synthesis of Cyclopropyl-Epothilone B Analogs and Studies Towards the Total Synthesis of Michaolide E.

Books Book Series Help; Contact Portal SYNTHESIS Full-text search Convergent Total Synthesis of (±)-Apomorphine via Benzyne Chemistry: (IMDAF) Approach towards the Synthesis of Isoindolo[2,1-a]quinazolines and Isoindolo[1,2-b]quinazolines Full Text. We report efforts towards a unified total synthesis of Korean sponge derived sesterterpenoids phorones A and B, using a biomimetic work has established a new synthetic approach to the parent ansellane sesterterpenoid skeleton with unanticipated diversion along a biogenetically related pathway.

Rhizoxin is an macrolide antibiotic isolated from the pathogenic plant fungus Rhizopus microsporus. It also exhibits antitumour and antimitotic activity. It has a role as an antineoplastic agent, a metabolite and an antimitotic. It is a macrolide antibiotic, an epoxide and a member of 1,3-oxazoles. Progress towards the total synthesis of namenamicin (1), the only enediyne antitumor antibiotic of marine origin, is reported. Two methods were investigated for the stereoselective introduction of the highly unusual quaternary C-4 center of the A-ring. Spirocyclic [3,3]-sigmatropic rearrangements of Cited by:


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Approaches towards a total synthesis of rhizoxin by Richard John Davenport Download PDF EPUB FB2

Total Synthesis of Leupyrrins A 1 and B 1, Highly Potent Antifungal Agents from the Myxobacterium Sorangium cellulosum. Chemistry - A European Journal23 (14), Cited by: The potential usefulness of 1, with its unique structural features has prompted our investigation of the total synthesis of 1, which had earlier resulted in the synthesis of the C-1 to C-9 segment.

In continuation of our efforts towards the total synthesis of 1, we report herein the first approach for the synthesis of the C to C segment 2 of rhizoxin (1).Cited by: An enantioselective synthesis of rhizoxin D (), isolated from the plant pathogenic fungus, is described.

The overall strategy is based on elaboration of the δ-lactone-substituted vinyl stannane and the phosphonate-substituted vinyl iodide, followed by their coupling to the core membered macrolide a. ChemInform Abstract: Approach Towards the Total Synthesis of Rhizoxin: Enantioselective Preparation of the Lactone Core Article in ChemInform 32(39) September with 20 Reads.

The total synthesis of rhizoxin D (1b) was achieved after transformation of 25 into the macro-lact and coupling the CC28 side chain using a Wittig-Wadsworth-Emmons reaction. Stereoselective Total Synthesis of Antitumor Macrolide (+)-Rhizoxin D†. Organic Letters6 (9), DOI: /olh.

Samir BouzBouz and, Janine Cossy. Stereoselective Synthesis of the C1−C13 Fragment of (+)-Discodermolide Using Asymmetric by: A novel approach towards the synthesis of the C1–C10 fragment of the biologically active antimitotic agent rhizoxin D is described.

The synthesis involves a stereoselective Michael addition reaction of lithium diallyl cuprate with an α,β-unsaturated six membered by: 4. The total synthesis of rhizoxin D (1b) was achieved after transformation of 25 into the macro-lact and coupling the CC28 side chain using a Wittig-Wadsworth-Emmons reaction.

View Show. Compound 4 was prepared in 21% overall yield from 7-butyrolactone. This synthesis utilizes pseudosymmetry about C(5), and this symmetry proved crucial in the preparation of this fragment. The use of 4 towards the total synthesis of rhizoxin is currently being pursued in our laboratories.

by: Quantitative DDQ removal23 of the para- methoxybenzyl ether produced the parent rhizoxin macrocycle Completion of the total synthesis of 2 was realized by oxidation of the allylic alco and Wittig olefination (, THF) with the carbanion generated from 4-[3-(diphenylphosphinoyl)methyl-propenyl]- 2-methyloxazole.9 The all-trans-triene was obtained in Cited by:   The new approach to the anticancer agent rhizoxin D described herein does not cohere with the conventional logic of metathesis, according to which macrocycles are best closed at a disubstituted olefinic site; rather, the trisubstituted C11−C12 alkene flanked by an allylic ‐OH group served as the pivot point for by: 4.

The sequence provided the desired aldehydes 49 and 50 as single isomers in good yields. Compiled spectroscopic data from the literature and present work provides evidence that the relative configuration of the methyl groups in the side chain of orevactaene may be 1,3-syn, which will be confirmed when the total synthesis has been by: The bacterial endosymbiont can be grown independently in culture.

This may allow easy harvesting of rhizoxin and the related compounds avoiding total chemical synthesis, although total chemical synthesis is possible. Cytotoxic function. Rhizoxin binds beta tubulin in eukaryotic cells disrupting microtubule Number: The remarkable biological properties of rhizoxin along with its unique structure3 have stimulated much interest in its synthesis, resulting in one total synthesis4 and several related synthetic studies.5 Our approach to rhizoxin features a convergent strategy that combines the two major fragments 2 and 3, each prepared from readily available Cited by: Fifty microliters of the diluted sample was added to each well, bringing the total volume per well to μl and yielding final concentrations of the rhizoxin analogs of 1, 5, 10, or 20 μg/ml.

Sterile dH 2 O and % (vol/vol) DMSO (corresponding to the highest concentration of DMSO in samples of rhizoxin analogs) served as controls. The Cited by: Enantioselective Total Synthesis of the Antitumor Macrolide Rhizoxin D Article in The Journal of Organic Chemistry 68(11) June with 14 Reads How we measure 'reads'.

Huperzine A and B are potent acetylcholinesterase inhibitors and promising against Alzheimer's disease. Completed and formal total syntheses of these medically relevant alkaloids are presented and discussed. Keywords: Huperzine A, huperzine B, total synthesis, alkaloids, Alzheimer’s disease Table of Contents 1.

Introduction 2. Huperzine A by: 2. A concise, protecting-group-free total synthesis of (−)-jiadifenolide, a synthetically challenging seco-prezizaane sesquiterpene with potent neurotrophic activity, is reported.

The convergent route features a SmI2/H2O-mediated stereoselective reductive cyclization, an unprecedented formal [4 + 1] annulative tetrahydrofuran-forming reaction and programmed redox by: Total Synthesis of (±)-Petasitolone and (±)-Fukinone, Srinivas Pasikanti, D.

Srinivas Reddy, Javed Iqbal, P. Dubey and Parthasarathi Das, SynthesisStudies toward the total synthesis of rhizoxin D: Stereoselective preparation of the CC19 fragment, Srinivas Padakanti, Chetlur Kirankumar, Ettam Ashok and Parthasarathi Das.

An efficient total synthesis of dysiherbaine, a potent and subtype-selective agonist for ionotropic glutamate receptors, has been achieved. Rhizoxin D (2) was synthesized from four subunits, A. A new synthetic strategy for the enantioselective synthesis of members of the dolabellane family of marine natural products has been demonstrated for the specific examples β-araneosene and isoedunol (1 and 2, respectively) by the pathway outlined in Scheme 1.

Key steps include (1) diastereoselective alkylation of Seebach's chiral lactate acetal (6) by the iodide derived from 5; (2 Cited by: Thieme E-Books & E-Journals. DE EN; Home Products. Journals Books Book Series A Cleaner Approach to Solid-Supported Radical Chemistry: Total Synthesis of Rhizoxin D Full Text HTML.Lycoposerramine A (1) is a pentacyclic alkaloid isolated in by Takayama and co-workers.A concise synthesis of a model compound 8 for the tetracyclic core of this natural product is described.

Key steps include the desymmetrising free-radical cyclisation of compound 7 to give compound 18 and spirocyclisation of compound 26 to give compound r approaches using a novel high-yielding.