Total Synthesis of the Protected Aglycon of Fidaxomicin (Tiacumicin B, Lipiarmycin A3)
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1 Total Synthesis of the Protected Aglycon of Fidaxomicin (Tiacumicin B, Lipiarmycin A3) H. Miyatake-Ondozabal, E. Kaufmann, K.Gademann* Angew. Chem. Int. Ed. 2015, 54, Literature Presentation Joséphine Cinqualbre
2 Introduction > Karl Gademann, born in 1972 Ph.D. at ETH under the supervision of Prof. Dr. Dieter Seebach ( ) Postdoctoral Fellow at Givaudan (2000) and in Harvard University with Prof. Dr. Eric N. Jacobsen ( ) Habilitation with Prof. Dr. Erick M. Carreira ( ) Full Professor and Dean of research at the University of Basel > Research Interests : Total synthesis of natural products Bioprospecting and Neuroengineering 2
3 Introduction > First isolation through fermentation of Actinoplanes deccanensis in 1975 by Parenti and co-workers > First antimicrobial agent approved by the FDA for the treatment of Clostridium difficile infection (2011, Optimer, Dificid ) > Bacterial activity against Mycobacterium tuberculosis > But low bioavailability and instability of the compound under acidic conditions > First total enantioselective synthesis : give access to structurally diverse analogues > Each year : 9 million new cases and 2 million deaths > Two drugs already developed Isoniazid Rifampicin A. Venugopal, S. Johnson, Clin. Infect. Dis. 2012, 54, ; W. Erb, J. Zhu, Nat. Prod. Rep. 2013, 30,
4 Retrosynthetic Analysis > 18-membered Macrolactone 2, central aglycon of fidaxomicin Short and highly convergent synthetic route Three main building blocks: vinyl iodide 3, vinyl stannane 4, and dienoic acid 5 Five chiral centers 4
5 Synthesis of building block 3 K. Ohata, S. Terashima, Chem. Pharm. Bull. 2009, 57, ; S. Kobayashi and co-workers, J. Am. Chem. Soc. 2004, 126, ; K. Kobayashi, Y. Fujii, I. Hayakawa, H. Kigoshi, Org. Lett.2011, 13,
6 Synthesis of building block 3 H. C. Brown, K. S. Bhat, R. S. Randad, J. Org. Chem. 1987, 52, ; 6
7 Synthesis of building block 4 J. D. White, M. Kang, B. G. Sheldon, Tetrahedron Lett. 1983, 24, ; K. C. O Brien, E. A. Colby, T. F. Jamison, Tetrahedron 2005, 61, ; 7
8 Synthesis of building block 5 T. Takeichi, M. Kuriyama, O. Onomura, Tetrahedron Lett. 2011, 52,
9 Synthesis of Macrolactone 2 CuTC A. Fürstner and coworkers, Angew. Chem. Int. Ed. 2006, 45, ; Yamaguchi esterification : N. M. Ahmad in Name Reactions for Functional Group Transformations (Eds.: J. J. Li, E. J. Corey), Wiley, Hoboken, NJ, 2007, pp
10 Synthesis of Macrolactone 2 K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, ; 10
11 Synthesis of Macrolactone 2 > Possible recycling of TES-deprotected product > Free hydroxy groups for following glycosylations 11
12 Conclusion > Synthesis in 18 steps via three main fragments in 0.7% yield > Stereoselective synthesis > Highlights of the strategy RCM for macrocyclization Diastereoselctive VMAR Stille coupling with sterically hindered substrates > Structures established the structures unambiguously > Preparation of the noviose, rhamnose and resorcinol units in progress 12
13 Other Synthesis > F. Glaus, K.-H. Altmann, Angew. Chem. Int. Ed. 2015, 54, ; 17 steps 0,1% yield 13
14 Other Synthesis > Synthesis fragment 6 K. Kubota, J. L. Leighton, Angew. Chem. Int. Ed. 2003, 42, ; H. Kim, S. Ho, J. L. Leighton, J. Am. Chem. Soc. 2011, 133,
15 Other Synthesis > W. Erb, J.-M. Grassot, D. Linder, L. Neuville, J. Zhu, Angew. Chem. Int. Ed. 2015, 54, steps % > To construct 5 : several oxidation/hwe/reduction sequence repeated use of Evan s copule and allylboration 15
16 Thank you for your attention! 16
17 Biosynthesis 17
18 Previous synthesis of resorcylic acid: M. Alexy, H.-D. Scharf, Liebigs Ann. Chem. 1991, ; W. Erb, J. Zhu, Nat. Prod. Rep. 2013, 30,
19 Previous synthetic studies on noviose: A. Klemer, M. Waldmann, Liebigs Ann. Chem. 1986, 2, ; 19
20 Synthesis evans auxilliary > Commercially available: TCI : 5g, 62 Aldrich : 5g, 249 CHF > Starting from (S)-phenylalanine J. R. Gage, D. A. Evans, Org. Synth. 1990, 68, 77 80; 20
21 Stereoselectivity 21
22 Removal of auxilliary 22
23 Sharpless epoxydation 23
24 Stille coupling 24
25 Stille coupling G. D. Allred, L.S. Liebeskind, J. Am. Chem. Soc. 1996, 118,
26 Hydrostannation 26
27 Monoselective TBDimethylsilylation T. Takeichi, M. Kuriyama, O. Onomura, Tetrahedron Lett. 2011, 52,
28 Corey Peterson olefination > Conversion Z to E with thiophenol 28
29 Stereoselective aldol reaction - Altmann 29
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