609358-96-5Relevant academic research and scientific papers
Total Synthesis and Structure Assignment of Saptomycin H
Shimura, Jun,Ando, Yoshio,Ohmori, Ken,Suzuki, Keisuke
supporting information, p. 1439 - 1443 (2022/03/01)
We report herein the first total synthesis of saptomycin H (2), by which the unidentified absolute stereochemistry of the oxiranyl side chain has been determined as 14R,16S. The keys include (1) concise assembly of three units, anthrone, sugar and side chain, and (2) AZADOL-mediated 6-endo-selective pyranone (A-ring) formation.
Total synthesis of thiostrepton. Retrosynthetic analysis and construction of key building blocks
Nicolaou,Safina, Brian S.,Zak, Mark,Lee, Sang Hyup,Nevalainen, Marta,Bella, Marco,Estrada, Anthony A.,Funke, Christian,Zecri, Frederic J.,Bulat, Stephan
, p. 11159 - 11175 (2007/10/03)
The first phase of the total synthesis of thiostrepton (1), a highly complex thiopeptide antibiotic, is described. After a brief introduction to the target molecule and its structural motifs, it is shown that retrosynthetic analysis of thiostrepton reveals compounds 23, 24, 26, 28, and 29 as potential key building blocks for the projected total synthesis. Concise and stereoselective constructions of all these intermediates are then described. The synthesis of the dehydropiperidine core 28 was based on a biosynthetically inspired aza-Diels-Alder dimerization of an appropriate azadiene system, an approach that was initially plagued with several problems which were, however, resolved satisfactorily by systematic investigations. The quinaldic acid fragment 24 and the thiazoline-thiazole segment 26 were synthesized by a series of reactions that included asymmetric and other stereoselective processes. The dehydroalanine tail precursor 23 and the alanine equivalent 29 were also prepared from the appropriate amino acids. Finally, a method was developed for the direct coupling of the labile dehydropiperidine key building block 28 to the more advanced and stable peptide intermediate 27 through capture with the highly reactive alanine equivalent 67 under conditions that avoided the initially encountered destructive ring contraction process.
Synthetic studies on thiostrepton: Construction of thiostrepton analogues with the thiazoline-containing macrocycle
Nicolaou,Nevalainen, Marta,Zak, Mark,Bulat, Stephan,Bella, Marco,Safina, Brian S.
, p. 3418 - 3424 (2007/10/03)
Leading the way: The novel thiostrepton analogue 1 and its 5S, 6S diastereomer were synthesized through macrolactamization reactions. Forays towards the total synthesis of the natural product itself should follow a similar strategy.
