S-Space College of Pharmacy (약학대학) Dept. of Manufacturing Pharmacy (제약학과) Theses (Ph.D. / Sc.D._제약학과)
강력한 항암 활성 Isocarbostyril 알칼로이드인 (+)-trans-Dihydronarciclasine의 입체선택적 전합성 : Stereoselective Total Synthesis of (+)-trans-Dihydronarciclasine, a Potent Anticancer Isocarbostyril Alkaloid
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- 약학대학 제약학과
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- 서울대학교 대학원
- Acid-mediated cyclization ; Antitumor agents ; Ireland-Claisen rearrangement ; Natural products ; Total synthesis
- 학위논문 (박사)-- 서울대학교 대학원 : 제약학과, 2014. 2. 김상희.
- We have achieved a highly stereoselective and efficient total synthesis of trans-dihydronarciclasine from a readily available chiral starting material. Our scheme defines two of the five stereogenic centers of the natural product by an amino acid ester-enolate Claisen rearrangement. The other three stereogenic centers are created in a highly stereocontrolled fashion via a six-membered-ring vinylogous ester intermediate, which is generated from the γ,δ-unsaturated ester functional group of Claisen rearrangement product in an efficient three-step sequence. This concise total synthesis exemplifies the use of a highly regioselective Friedel-Crafts-type cyclization to form the B-ring via an isocyanate intermediate derived from an N-Boc group, which is superior to the conventional method using an imino triflate intermediate. This mild and regioselective reaction conditions are also applicable for synthesis of various substituted isoquinolin-1-ones, β-carbolines, thiophen fused ring systems and tetrahydrobenzoazepin-1-ones. Acid additives, such as BF3•Et2O, extend the application of the method to substrates bearing less nucleophilic aryl moieties by enhancing the Friedel-Crafts-type cyclization of isocyanate intermediates.
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