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제 목 : Functionalized Small & Medium Carbocycles
연 사 : 권용훈 교수(서울대학교 응용생물화학부)
일 시 : 2019년 10월 31일(목) 오후 4시 30분
장 소 : 화학관 2층 서병인강의실 (330226호실)
Functionalized Small & Medium Carbocycles
Department of Applied Biology and Chemistry
Seoul National University, Seoul 08826, Korea
The development of ring closing alkyne metathesis (RCAM) followed by stereoselective reduction of the resulting alkyne has rendered opportunities to access macrolides as well as medium-sized carbocycles bearing Z- or E-alkenes.1 Beyond the selective formation of (Z)- or (E)-disubstituted alkenes, we recently demonstrated that a macrolide having a trisubstituted alkene with well-defined stereochemistry can be prepared by a RCAM/trans-selective hydrostannation sequence. This approach is complementary to ring closing alkene metathesis (RCM) since (stereoselective) formation of trisubstituted alkenes by RCM is problematic. Testing this method in the total synthesis of a complex natural product is desirable to broaden the generality of the strategy. Disciformycins A and B, isolated from cultures of Pyxidicoccus fallax by the Müller group in 2014,2 were chosen as our targets as they exhibit considerable antibacterial activity against Gram-positive bacteria. This presentation will describe details of unforeseen synthetic challenges and our endeavors to resolve these problems met along the way.3
1. Fürstner, A. Angew. Chem. Int. Ed. 2013, 52, 2794–2819.
2. Surup, F.; Viehrig, K.; Mohr, K. I.; Herrmann, J.; Jansen, R.; Mülller, R. Angew. Chem. Int. Ed. 2014, 53, 13588–13591.
3. Kwon, Y.; Schulthoff, S.; Dao, Q. M.; Wirtz, C.; Fürstner, A. Chem. Eur. J. 2018, 24, 109 –114.