92418-72-9Relevant academic research and scientific papers
Total Synthesis of the Marine Macrolide Amphidinolide F
Ferrié, Laurent,Fenneteau, Johan,Figadère, Bruno
supporting information, p. 3192 - 3196 (2018/06/11)
A new and efficient convergent approach toward the synthesis of amphidinolide F is described through the assembly of three fragments. The two trans-tetrahydrofurans were built by a diastereoselective C-glycosylation with titanium enolate of bulky N-acetyloxazolidinethiones. The side chain was inserted by a Liebeskind-Srogl cross-coupling reaction. A sulfone condensation/desulfonylation sequence, a Stille cross-coupling, and a macrolactonization were applied to connect the fragments.
First total synthesis of fuzanins C, D and their analogues as anticancer agents
Kumar, S. Naveen,Pavan Kumar, C. H. N. S. Sai,Srihari,Kancharla, Sravani,Srinivas, Kolupula,Shrivastava, Shweta,Naidu,Jayathirtha Rao
, p. 8365 - 8375 (2014/02/14)
The first total synthesis of fuzanins C and D, isolated from the culture supernatant of Kitasatospora sp. IFM10917, is described. Key features of this synthetic strategy involve the use of Sharpless asymmetric epoxidation, dihydroxylation, Mitsunobu reaction and Julia-Kocienski olefination. The total synthesis reported herein also confirmed the absolute configuration of fuzanin D. The optical rotations of synthesized fuzanin D and natural product were opposite in sign, leading to a revision of the reported structure as its enantiomer which is further confirmed by molecular modeling studies. In addition, we also synthesized the analogues of fuzanins C, D containing the quinoline nucleus. All of the synthesized compounds were screened for anticancer activity on four cell lines and found to be potent against HT29 colon cancer cell lines, whereas they were found to be less potent against cervical and breast cancer cell lines.
Studies for the total synthesis of amphidinolide P
Williams, David R.,Myers, Brian J.,Mi, Liang,Binder, Randall J.
, p. 4762 - 4778 (2013/07/05)
A convergent, enantiocontrolled total synthesis of the 15-membered macrolide, amphidinolide P, is described. The synthesis utilizes three nonracemic components for an efficient assembly of the macrolactone in 12 steps via the longest linear pathway. Key developments include studies of the Hosomi-Sakurai reaction for the formation of the C6-C7 bond, a "ligandless" palladium-mediated Stille cross-coupling of the vinylic stannane 4 and the alkenyl bromide 5 to produce a highly functionalized dienol, and a thermally induced, intramolecular lactonization via the late-stage formation of an intermediate α-acylketene.
Development and application of versatile bis-hydroxamic acids for catalytic asymmetric oxidation
Barlan, Allan U.,Zhang, Wei,Yamamoto, Hisashi
, p. 6075 - 6087 (2008/02/03)
In this article, we describe the development and preliminary results of our new designed C2-symmetric bis-hydroxamic acid (BHA) ligands and the application of the new ligands for vanadium-catalyzed asymmetric epoxidation of allylic alcohols as well as homoallylic alcohols. From this success we demonstrate the versatile nature of BHA in the molybdenum catalyzed asymmetric oxidation of unfunctionalized olefins and sulfides.
Enantioselective epoxidation of allylic alcohols by a chiral complex of vanadium: An effective controller system and a rational mechanistic model
Zhang, Wei,Basak, Arindrajit,Kosugi, Yuji,Hoshino, Yujiro,Yamamoto, Hisashi
, p. 4389 - 4391 (2007/10/03)
(Chemical Equation Presented) Bishydroxamic acid derivatives are used as ligands for a vanadium catalyst in the preparation of epoxy alcohols (see scheme). The methodology uses aqueous tert-butyl hydroperoxide (TBHP) as an achiral oxidant, low catalyst loading, low reaction temperatures (0°C to room temperature), and simple workup procedures. The reaction is applied to the kinetic resolution of a secondary allylic alcohol and the preparation of small epoxy alcohols. R1, R2, R3: alkyl, aryl, H.
BUTYRATE METABOLISM IN STREPTOMYCETES. CHARACTERIZATION OF AN INTRAMOLECULAR VICINAL INTERCHANGE REARRANGEMENT LINKING ISOBUTYRATE AND BUTYRATE IN STREPTOMYCES CINNAMONENSIS
Reynolds, Kevin A.,O'Hagan, David,Gani, David,Robinson, John A.
, p. 3195 - 3208 (2007/10/02)
The incorporations of varicus carbon-13 and deuterium labelled forms of isobutyrate into the polyether antibiotic monensin-A have provided evidence for the existence of a novel rearrangement in whole cells of Streptomyces cinnamonensis, which leads to the conversion of isobutyrate into butyrate.This rearrangement is shown to proceed in an intramolecular fashion by migration of the carboxy carbon of isobutyrate to the 2-pro-S methyl, with a concomitant back migration of a hydrogen atom from this methyl group predominantly into the 3-pro-R position in butyrate.Formally, therefore, the carboxy carbon is replaced with overall retention of configuration, in a vicinal interchange rearrangement.The significance of these observations with regard to the coenzyme requirements of the rearrangement, and its relationship to polyether and macrolide antibiotic production in Streptomycetes is discussed.
