The Chiral Synthesis of the Lucentamycins A-D Core, 3-Methyl -4-Ethylideneproline
- The Chiral Synthesis of the Lucentamycins A-D Core, 3-Methyl -4-Ethylideneproline
- 유하나; 최환근; 하정미; 심태보
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- 대한화학회 학술대회
- Lucentamycins A-D were isolated in 2007 from the Marine-Derived Actinomycete Nocardiopsis lucentensis by Cho and co-workers. It turned out that Lucentamycin A and B possess anti-proliferative activity on HCT-116 with IC50 value of 0.20 and 11 uM respectively. Interestingly, Lucentamycin C and D did not exhibit growth inhibitory activity against HCT-116, human colon cancer cell even at 150 uM concentration. Our research group has been most recently interested in identifying molecular target protein of Lucentamycin A and B in cancer cells. To achieve this goal we have embarked to synthesize effectively 3-methyl-4-ethylideneproline, the core structure of Lucentamycins starting from (L)-methionine. This synthesis has successfully been accomplished by adopting rhodium catalyzed cyclization reaction of a 1,6-enyne in efficient and stereoselective manner.
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