90192-97-5Relevant academic research and scientific papers
A carbohydrate approach for the formal total synthesis of (?)-aspergillide C
Srihari, Pabbaraja,Krishna, Namballa Hari,Sridhar, Ydhyam,Kamal, Ahmed
, p. 3122 - 3126 (2014)
An enantioselective formal total synthesis of aspergillide C is accomplished using commercially available tri-O-acetyl-D-galactal employing a Ferrier-type C-glycosylation, utilizing a Trost hydrosilylation and protodesilylation as key reactions.
Synthesis and biological evaluation of 12-, 13-, 14-membered macrolides and open chain 2,6-trans-disubstituted dihydropyran analogues for aspergillides
Pabbaraja, Srihari,Gantasala, Naresh,Ydhyam, Sridhar,Namballa, Hari Krishna,Gundeboina, Subhashini,Lambu, Mallikharjuna R.,Meena, Sanjeev,Datta, Dipak
, p. 2570 - 2576 (2018/05/30)
Stereoselective synthesis of twenty (three 12-, five 13- and twelve 14-membered) macrolides and seventeen functionalized 2,6-trans-disubstituted dihydropyran derivatives have been achieved. The key reactions include an Achmatowicz rearrangement, Ferrier-type alkynylation, Yamaguchi macrolactonization and Lindlar's hydrogenation. Biological screening of the synthesised compounds showed moderate activity against human cancer cell-lines.
Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A
Sommer, Heiko,Fürstner, Alois
supporting information, p. 3210 - 3213 (2016/07/13)
Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoich
Stereodivergent total synthesis of (+)-aspergillide B and (+)-7-epi-aspergillide A
Sridhar,Srihari
, p. 578 - 587 (2013/02/26)
The stereoselective total syntheses of (+)-aspergillide B and (+)-7-epi-aspergillide A were achieved. The key reactions include Noyori's asymmetric transfer hydrogenation, an Achmatowicz rearrangement, a Ferrier-type alkynylation, a hydrosilylation-protodesilylation, a CBS (Corey-Bakshi-Shibata) oxazaborolidine reduction, a Yamaguchi macrolactonization, and a Mitsunobu macrolactonization. The stereoselective total syntheses of (+)-aspergillide B and (+)-7-epi-aspergillide A were achieved. The key reactions include Noyori's asymmetric transfer hydrogenation, an Achmatowicz rearrangement, a Ferrier-type alkynylation, a hydrosilylation-protodesilylation, a CBS (Corey-Bakshi-Shibata) oxazaborolidine reduction, a Yamaguchi macrolactonization, and a Mitsunobu macrolactonization. Copyright
Stereoconvergent synthesis of the C1-C11 and C12-C24 fragments of (-)-macrolactin-A
Yadav,Raj Kumar,Sabitha
, p. 463 - 466 (2008/09/18)
Stereoconvergent syntheses of the C1-C11 and C12-C24 fragments of (-)-macrolactin-A are reported.
Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp.
Burgess, Kevin,Jennings, Lee D.
, p. 6129 - 6139 (2007/10/02)
Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of β-hydroxy-α-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of γ-hydroxy-α,β-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.
Synthesis of Z,Z-Skipped Diene Macrolide Pheromones for Cryptolestes and Oryzaephilus Grain Beetles (Coleoptera Cucujidae)
Millar, Jocelyn G.,Oehlschlager, Allan C.
, p. 2332 - 2338 (2007/10/02)
Three macrolide aggregation pheromones for Cryptolestes pusillus, Cryptolestes turcicus, and Oryzaephilus mercator were synthesized stereoselectively from acyclic precursors.The first, 13-methyl-(5Z,8Z)-tridecadienolide (I), is an aggregation pheromone for C. turcicus and had been tentatively identified previously in Phoracantha synonyma.The second, 11-methyl-(3Z,6Z)-undecadienolide (II), is an aggregation pheromone for O. mercator.The third, (3Z,6Z)-dodecadienolide (III) is an aggregation pheromone for O. mercator and is also slightly attractive to C. pusillus.The racemic and enantiomeric forms of I were synthesized.
