194342-84-2Relevant articles and documents
Total Synthesis of Kalimantacin A
Davies, Jonathan A.,Bull, Freya M.,Walker, Paul D.,Weir, Angus N. M.,Lavigne, Rob,Masschelein, Joleen,Simpson, Thomas J.,Race, Paul R.,Crump, Matthew P.,Willis, Christine L.
, p. 6349 - 6353 (2020/09/02)
The kalimantacins make up a family of hybrid polyketide-nonribosomal peptide-derived natural products that display potent and selective antibiotic activity against multidrug resistant strains of Staphylococcus aureus. Herein, we report the first total synthesis of kalimantacin A, in which three fragments are prepared and then united via Sonogashira and amide couplings. The enantioselective synthetic approach is convergent, unlocking routes to further kalimantacins and analogues for structure-activity relationship studies and clinical evaluation.
A highly stereoselective formal synthesis of hapalosin
Kumar, Harish,Reddy, A. Srinivas,Yadav,Reddy, B. V. Subba
, p. 1415 - 1419 (2013/07/26)
A flexible and highly diastereoselective formal synthesis of hapalosin, a cyclodepsipeptide isolated from the blue green alga Hapalosiphon welwitschii and having multidrug-resistance-reversing activity is described. The synthetic route involves the addition of organometallic reagent to N-tert- butanesulfinylimine, Jung nonaldol aldol reaction, and Yamaguchi esterification as key steps. Georg Thieme Verlag Stuttgart · New York.
Enantioselective synthesis of structurally intricate and complementary polyoxygenated building blocks of spongistatin 1 (altohyrtin a)
Braun, Alain,Cho, Ii Hwan,Ciblat, Stephane,Clyne, Dean,Forgione, Pat,Hart, Amy C.,Huang, Guoxiang,Kim, Jungchul,Modolo, Isabelle,Paquette, Leo A.,Peng, Xiaowen,Pichlmair, Stefan,Stewart, Catherine A.,Wang, Jizhou,Zuev, Dmitry
experimental part, p. 651 - 769 (2010/02/27)
Enantioselective approaches to the construction of four complex building blocks of the structurally intricate marine macrolide known as spongistatin 1 are presented. The first phase of the synthetic effort relies on a practical approach to a desymmetrized, enantiomerically pure spiroketal ring system incorporating rings A and B. Concurrently, the C17-C28 subunit, which houses one-fifth of the stereogenic centers of the target in the form of rings C and D, was assembled via a composite of stereocontrolled aldol condensations. Once arrival at the entire C1-C28 sector had been realized, routes were devised to provide two additional highly functionalized sectors consisting of C29-C44 and C38-C51. A series of subsequent transformations including cyclization of the E ring and hydroboration to afford the B-alkyl intermediate for the key Suzuki coupling to append the side chain took advantage of efficient stereocontrol. Ultimately, complete assembly and functionalization of the western EF sector of spongistatin was thwarted by an inoperative Suzuki coupling step intended to join the side chain to the C29-C44 sector, and later because of complications due to protecting groups, which precluded the complete elaboration of the late stage C29-C51 intermediate.
