31077-20-0Relevant academic research and scientific papers
MACROLIDES AND METHODS OF THEIR PREPARATION AND USE
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, (2014/10/18)
Provided herein are methods of preparing macrolides by the coupling of an eastern and western half, followed by macrocyclization, to provide macrolides, including both known and novel macrolides. Intermediates in the synthesis of macrolides including the eastern and western halves are also provided. Pharmaceutical compositions and methods of treating infectious diseases and inflammatory conditions using the inventive macrolides are also provided. A general diastereoselective aldol methodology used in the synthesis of the western half is further provided.
Total synthesis of (+)-ambruticin S: Probing the pharmacophoric subunit
Hanessian, Stephen,Focken, Thilo,Mi, Xueling,Oza, Rupal,Chen, Bin,Ritson, Dougal,Beaudegnies, Renaud
experimental part, p. 5601 - 5618 (2010/11/03)
An enantioselective synthesis of the antifungal natural product (+)-ambruticin S has been accomplished starting with the readily available methyl α-d-glucopyranoside, (R)-Roche ester, and (S)-glycidol as chirons, which encompassed seven of the 10 stereogenic centers of the target molecule. The remaining three centers were set by a highly diastereoselective, asymmetric cyclopropanation employing a chiral, nonracemic phosphonamide reagent. Our strategy for the construction of the dihydropyran subunit involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization. Other key steps in the synthesis featured an epoxide opening with a dithiane anion, two efficient phosphonamide-anion based olefinations, and a late-stage C-glycosylation.
Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 17: Synthesis and opening reactions of cis- and trans-oxides derived from (2S,6R)-2-benzyloxy-6-methyl-3,6-dihydro-2H-pyran, (2R,6R)- and (2S,6R)-2-methoxy-6-m
Crotti, Paolo,Di Bussolo, Valeria,Favero, Lucilla,Macchia, Franco,Pineschi, Mauro
, p. 6069 - 6091 (2007/10/03)
The regiochemical behavior of the title deoxy anhydrosugars, prepared in an enantioselective way starting from methyl α-D-glucopyranoside, was examined in opening reactions, both under standard and chelating conditions. The results clearly indicate the in
Milbemycin Synthesis: Asymmetric Synthesis of Spiroketals from Methyl α-D-Glucopyranoside
Khandekar, Girish,Robinson, Gareth C.,Stacey, Nicholas A.,Thomas, Eric J.,Vather, Sunil
, p. 1507 - 1520 (2007/10/02)
The 6-chloro-4,6-dideoxygalactoside 8 was prepared by selective dichlorination of methyl α-D-glucopyranoside 6 followed by hydrogenolysis, and was converted into the epoxyalkyldithioacetal 10 by treatment with propane-1,3-dithiol, protection, and formation of the epoxide.With nucleophiles, the epoxyalkyldithioacetal underwent opening of the epoxide, whereas with strongly basic reagents abstraction of the dithiane proton at C-2 followed by elimination gave the epoxy hydroxy ketone dithioacetal 34.This chemistry was used to prepare a series of anti-1,3-diols 36, 38 and 40 and should be useful for natural-product synthesis.Using the vinyllithium reagent derived from iodide 57, the diol 60 corresponding to the C(11)-C(21) fragment of milbemycin E 1 was prepared, and this was taken through to the spiroketal 64 as a model for a proposed synthesis of the C(11)-C(25) fragment of a milbemycin.The anti-diols 36 and 40 were taken through to the spiroketals 74 and 69, respectively, so providing an asymmetric synthesis of fully functionalised milbemycin spiroketals.
Asymmetric Synthesis of the Spiroacetal Fragment of Milbemycin E
Khandekar, Girish,Robinson, Gareth C.,Stacey, Nicholas A.,Steel, Patrick G.,Thomas, Eric J.,Vather, Sunil
, p. 877 - 880 (2007/10/02)
Spiro-acetals (17) and (21) have been synthesized from methyl α-D-glucopyranoside (11), via the 6-chloro-4,6-dideoxygalactopyranoside (10), the epoxy-dithiane (8), and the open-chain dithianes (16) and (20).
