1. A formal total synthesis of frondosin A 2. studies toward the efficient asymmetric total synthesis of apicularen A and its analogues = 1. 프론도신 A의 전합성에 관한 연구 2. 애피큘라렌 A와 그 유도체들의 효율적인 비대칭 전합성에 관한 연구

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(+)-Frondosin A is a member of a family of five norsesquiterpenoid (14-carbon) natural products, frondosins A-E, which were originally extracted from the marine sponge Dysidea frondosa. And It has unique structures which are exocyclic olefin and neighboring two syn substituents. The frondosins inhibit the binding of interleukin-8, and IL-8 receptor antagonist is a promising target for development of novel anti-inflammatory agents. Frondosin A was found to be the most potent of the frondosins. In addition, the frondosins have been shown to exhibit anti-HIV activity. Cycloaddition reactions, which can make two new bonds in region- and streocontrolled fashion, are very useful methods in organic synthesis. Among the various types of cycloadditions, dipolar cycloadditions of oxidopyrylium species and the related carbonyl yilides have proved to be a powerful methodology for the synthesis. The intramolecular [5+2] cycloaddition reaction of oxidopyrylium ion generated from acetoxypyranone produced fused 6 and 7-membered ring regio- and stereoselectivity. This method provides a good synthetic strategy to construct norsesquiterpenoid core structure like biologically active frondosins. Asymmetric total synthesis of frondosin A, which is fused 6 and 7-membered ring and cis- phenyl and contain methyl functional group, was successful utilized regio- and stereoselectively by using oxidopyrylium [5+2] cycloaddition. Coupling of three fragments was achieved by olefin methathesis and alkylation reaction. Key intermediate was constructed by oxidopyrylium [5+2] cycloaddition reaction. Trost’s intermediate was completed through several steps. Apicularen A is highly cytostatic to a wide range of human cancer cell lines. Recent reports indicated that (-)-apicularen A exhibited antiangiogenesis properties, induced apoptosis, produced nitric oxide, acted as a novel specific V-ATPase inhibitor. And this compound have unique structural features which are macrocyclic salicylate ester co...
Advisors
Lee, Hee-Yoonresearcher이희윤
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
2014
Identifier
568651/325007  / 020098009
Language
eng
Description

학위논문(박사) - 한국과학기술원 : 화학과, 2014.2, [ iv, 117 p. ]

Keywords

oxidopyrylium; 락톤형성반응; 엔-아인 반응; 옥시도피릴륨; 애피큘라렌; 프론도신; frondosin; enyne reaction; lactonization; apicularen

URI
http://hdl.handle.net/10203/196460
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=568651&flag=dissertation
Appears in Collection
CH-Theses_Ph.D.(박사논문)
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