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제122회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Study for total synthesis of (-)-platensimycin by Intramolecular Diels-Alder of 2-pyrone

2018년 8월 30일 16시 22분 42초
ORGN.P-270 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 18일 (목요일) 11:00~12:30
Organic Chemistry
저자 및
Hyo-mi Kim, Cheon-Gyu Cho*
Department of Chemistry, Hanyang University, Korea

We have investigated 3,5-dibromo-2-pyrone towards target-oriented synthesis, utilizing its peculiar reactivity as a neutral diene and the selective maneuverability of the two bromine groups. Such efforts have allowed syntheses of a serious bioactive natural products.1 Inspired by our recent success on internal hydrogen bonding mediated asymmetric Diels-Alder reaction, we have launched a program inventing a new synthetic strategy to (-)-platensimycin. Included in the new route are C3-selective Stille-coupling reaction of 3,5-dibromo-2-pyrone, chemo-selective hydrogenation and intramolecular Diels-Alder cyclization. Presented herein is our recent progress toward total synthesis of (-)-platensimycin. Reference 1. (a) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288. (b) Tam. N. T.; Cho, C.-G. Org. Lett. 2007, 9, 3391. (c) Shin, I.-J.; Choi, E.-S.; Cho, C.-G. Angew. Chem. Int. Ed. 2007, 46, 2303. (d) Chang, J. H.; Kang, H.-U.; Jung, I.-H.; Cho, C.-G. Org. Lett. 2010, 12, 2016. (e) Jung, Y.-G.; Kang, H.-U.; Cho, H.-K.; Cho, C.-G. Org. Lett. 2011, 13, 5890. (f) Jung, Y.-G.; Lee, S.-C.; Cho, H.-K.; Nitin B. D.; Song, J.-Y.; Cho, C.-G. Org. Lett. 2013, 15, 132. (g) Cho, H.-K.; Lim, H.-Y.; Cho, C.-G. Org. Lett. 2013, 15, 5806. (g) Shin. H.-S.; Jung. Y.-G.; Cho. H.-K.; Park. Y.-G.; Cho. C.-G. Org. Lett. 2014, 16, 5718.