114458-03-6Relevant articles and documents
Structural and Functional Analysis of Bacterial Sulfonosphingolipids and Rosette-Inducing Factor 2 (RIF-2) by Mass Spectrometry-Guided Isolation and Total Synthesis
Beemelmanns, Christine,Jautzus, Theresa,King, Nicole,Leichnitz, Daniel,Peng, Chia-Chi,Ragu?, Luka,Regestein, Lars,Rutaganira, Florentine U. N.
supporting information, (2022/01/04)
We have analyzed the abundance of bacterial sulfonosphingolipids, including rosette-inducing factors (RIFs), in seven bacterial prey strains by using high-resolution tandem mass spectrometry (HRMS2) and molecular networking (MN) within the Glob
A Unified Approach to Phytosiderophore Natural Products
Kratena, Nicolas,G?kler, Tobias,Maltrovsky, Lara,Oburger, Eva,Stanetty, Christian
supporting information, p. 577 - 580 (2020/11/02)
This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.
Synthesis of Saxitoxin and Its Derivatives
Chida, Noritaka,Kinoshita, Kyoko,Mukai, Shori,Okamoto, Ryosuke,Okuyama, Yuya,Sato, Takaaki
supporting information, (2020/11/13)
The chiral synthesis of (+)-saxitoxin and its derivatives is described. Two consecutive carbon-nitrogen bonds at C-5 and C-6 in saxitoxin were effectively installed by the sequential Overman rearrangement of an allylic vicinal diol derived from d-malic acid. The bicyclic guanidine unit was constructed by the intramolecular aminal formation of an acyclic bis-guanidine derivative possessing a ketone carbonyl at C-4. From the bicyclic aminal intermediate, (+)-saxitoxin, (+)-decarbamoyl-β-saxitoxinol [(+)-dc-β-saxitoxinol], and the unnatural skeletal isomer, (-)-iso-dc-saxitoxinol, were synthesized.