69779-57-3Relevant academic research and scientific papers
Total synthesis of (-)-4,8,10-tridesmethyl telithromycin
Velvadapu, Venkata,Paul, Tapas,Wagh, Bharat,Glassford, Ian,Debrosse, Charles,Andrade, Rodrigo B.
scheme or table, p. 7516 - 7527 (2011/11/29)
Novel sources of antibiotics are required to address the serious problem of antibiotic resistance. Telithromycin (2) is a third-generation macrolide antibiotic prepared from erythromycin (1) and used clinically since 2004. Herein we report the details of
Stereoselective formal total synthesis of (+)-methynolide
Yadav,Pratap,Rajender
, p. 5882 - 5885 (2008/02/09)
(Chemical Equation Presented) A highly stereoselective and convergent formal total synthesis of (+)-methynolide is described. The salient features of this synthesis have been the construction of the C1-C7 and C8-C11fragments via a desymmetrization approach, Sharpless asymmetric epoxidation of an allyl alcohol, respectively, and linkage of both the fragments by Nozaki-Hiyama-Kishi reaction.
Total Synthesis of Preaurovertin, Putative Biogenetic Precursor of Aurovertin. Biosynthetic Interrelationships between the Aurovertins, Citreoviridinols and Asteltoxin
Forbes, Judith E.,Pattenden, Gerald
, p. 1959 - 1966 (2007/10/02)
A number of complementary biomimetic approaches to the tetrahydrofuranyl portion of the dienal 13, which was used in a synthesis of preaurovertin, are described.Epoxidation of the trienoate 31 produces largely the β-epoxide 32, which on treatment with aqueous trifluoroacetic acid undergoes deacetalisation and concomitant cyclisation leading to compound 34.After conversion of 34 into dienal 13, a Wittig reaction with the ylide derived from the phosphonium salt 37 produces preaurovertin.Preaurovertin is a putative biogenetic precursor of aurovertin found in Calcarisporium arbuscula.Citreoviridin produced by Penicillium citreoviride relates to preaurovertin, and the citreoviridinols are related structurally to aurovertin.In addition, aurovertin is related biogenetically to asteltoxin found in Aspergillus stellatus.These structural and biosynthetic interrelationships are considered alongside the synthetic work.
Short Enantioselective Approach to a Building Block for Macrolide Syntheses
Stuermer, Rainer
, p. 311 - 313 (2007/10/02)
The protected α,β-dihydroxy aldehyde 2, a key building block for several macrolide antibiotics, has been synthesized from the epoxy alcohol 6.Oxidation furnishes the corresponding aldehyde 7, which is acetalized with ketones in the presence of SnCl4, with
SUBSTRATE SPECIFICITY AND ENANTIOSELECTIVITY OF PENICILLINACYLASE CATALYZED HYDROLYSIS OF PHENACETYL ESTERS OF SYNTHETICALLY USEFUL CARBINOLS
Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Lazzarini, Ameriga,Casati, Paolo
, p. 2575 - 2582 (2007/10/02)
Penicillinacylase from E. coli, immobilized on Eupergit C beads catalyzes the hydrolysis in water/CH3CN 10:1, at pH 7.5 and 23 deg C, of a set of O-phenylacetate esters of primary carbinols.The highest enantioselectivity is observed in the case of the 2,2-dimethyl-1,3-dioxolane-4-methanols structurally related to the penicillin (1) framework.Minor modifications of this basic structure are not altering the acceptability by the enzyme, but significantly decrease the enantioselectivity of the hydrolysis, as does the use of benzene as solvent and Sepharose-bound enzyme.
EPOXIDES IN SYNTHESIS. STUDIES TOWARDS THE AUROVERTINS
Forbes, Judith E.,Pattenden, Gerald
, p. 2771 - 2774 (2007/10/02)
A synthesis of the 2,6-dioxabicyclooctane ring system (16) found in the natural aurovertins e. g. (1), based on a biogenetic model (Scheme 1) and using two key epoxide cyclisation steps viz (12) (13) and (14) (16a), is described.
Enantioselective Syntheses using Chiral Epoxy-alcohols
Colvin, Ernest W.,Robertson, Alan D.,Wakharkar, Shaila
, p. 312 - 314 (2007/10/02)
The epoxy-alcohol (1, R=CH2Ph) opens under acid catalysis by attack at the proximate carbon atom.
