176199-99-8Relevant academic research and scientific papers
Asymmetric Total Synthesis of the Complex Polycyclic Xanthone FD-594
Chen, Kuanwei,Gao, Shuanhu,He, Haibing,Xie, Tao,Zheng, Chaoying
, p. 4360 - 4364 (2020)
A highly convergent approach was developed to achieve the first asymmetric and scalable total synthesis of FD-594, a complex polycyclic xanthone natural product from Streptomyces sp. TA-0256, in a longest linear sequence (LLS) of 20 steps. The trans-9,10-
Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach
Yalamanchili, Subbarao,Lloyd, DIna,Bennett, Clay S.
supporting information, p. 3674 - 3677 (2019/05/17)
The synthesis of the hexasaccharide fragment of landomycin A is reported. Using p-toluenesulfonyl chloride mediated dehydrative glycosylation, we constructed the deoxy-sugar linkages in a stereoselective fashion without the need for temporary prosthetic g
SMALL MOLECULE COMPOUNDS SELECTIVE AGAINST GRAM-NEGATIVE BACTERIAL INFECTIONS
-
Paragraph 0436; 0441, (2016/01/30)
The described invention provides fully synthetic, biologically active mangrolide A. It describes schemes to chemically synthesize mangrolide A, intermediates and analogs of mangrolide A, and their antibacterial activity.
Combinatorial synthesis of deoxyhexasaccharides related to the landomycin a sugar moiety, based on an orthogonal deprotection strategy
Tanaka, Hiroshi,Yamaguchi, Sho,Yoshizawa, Atsushi,Takagi, Motoki,Shinya, Kazuo,Takahashi, Takashi
experimental part, p. 1407 - 1424 (2011/08/10)
In this report, we describe the stereoselective synthesis of a combinatorial library comprised of 16 de- oxyhexasaccharides that are related to a landomycin A sugar moiety, based on an orthogonal deprotection strategy. The use of an olivosyl donor contain
Total synthesis of everninomicin 13,384-1 - Part 1: Retrosynthetic analysis and synthesis of the A1B(A)C fragment
Nicolaou,Rodriguez, Rosa Maria,Mitchell, Helen J.,Suzuki, Hideo,Fylaktakidou, Konstantina C.,Baudoin, Olivier,Van Delft, Floris L.
, p. 3095 - 3115 (2007/10/03)
In this first of a series of four articles we introduce everninomicin 13,384-1 (1), a powerful antibiotic effective against drug resistant bacteria, as a target for total synthesis and discuss its retrosynthetic analysis. From the three defined fragments required for the synthesis (2: A1B(A)C fragment; 4: DE fragment; 5: FGHA2 fragment), we describe herein two approaches to the A1B(A)C block. The first strategy relied on an olefin metathesis reaction to construct a common intermediate for rings B and C, but was faced with final protecting group problems. The second, and successful approach, involved a 1,2-phenylsulfeno migration and a sulfur directed glycosidation procedure to link rings B and C, as well as an acyl fluoride intermediate to install the sterically hindered aryl ester moiety (ring A1). The final stages of the synthesis of the required 2-phenylseleno glycosyl fluoride 2 required introduction of a phenylseleno group at C-1 of ring C followed by a novel, DAST-promoted 1,2-migration to produce the desired 2-β-phenylseleno glycosyl fluoride moiety.
Total synthesis of everninomicin 13,384-1 - Part 1: Synthesis of the A1B(A)C fragment
Nicolaou,Mitchell, Helen J.,Suzuki, Hideo,Rodriguez, Rosa Maria,Baudoin, Olivier,Fylaktakidou, Konstantina C.
, p. 3334 - 3339 (2007/10/03)
The powerful antibiotic everninomicin 13,384-1 (1, Ziracin) has been prepared for the first time through a total synthesis. The (1 → 1-disaccharide and the two orthoesters of this target molecule were introduced by new methodologies using a tin acetal and 1,2-phenylseleno migrations. The reaction sequence also relies on stereoselective glycosidations and subtle manipulations of protecting groups. In addition to the introduction of new synthetic methodologies, this total synthesis should allow the preparation of combinatorial libraries of semisynthetic analogues of this highly promising antibiotic for biological screening purposes.
Iodonium ion-assisted synthesis of a tetrameric fragment corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovar I
Zegelaar-Jaarsveld, Korien,Smits, Sander A. W.,Van Straten, Nicole C. R.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 3593 - 3608 (2007/10/03)
Two procedures are described towards the assembly of the tyramine spacer-containing tetramer 5, a derivative of the phenolic glycolipid of Mycobacterium kansasii serovar I. First, iodonium ion-mediated glycosylation of trimeric acceptor 2a with D-rhamnopyranoside donor 10 gave fully protected tetramer 17. Selective removal of the chloroacetyl group of 17, subsequent deoxygenation and removal of the protective groups, led to target 5. The potential occurrence of double stereodifferentiation (DSD) was examined by condensation of L-fucopyranoside model acceptor 14 with both the enantiomeric rhamnopyranoside donors 10 and 13. The second procedure involves elongation of trimeric acceptor 2b with 6-deoxy-D-glucopyranoside 28. Desulfurisation of the resulting tetrameric fragment 36 followed by hydrogenation of 37 gave 38, the phenylacetyl (PhAc) of which was enzymatically removed to yield target tetramer 5.
