222 0

Full metadata record

DC FieldValueLanguage
dc.contributor.advisor조천규-
dc.contributor.author이준호-
dc.date.accessioned2020-02-11T04:35:35Z-
dc.date.available2020-02-11T04:35:35Z-
dc.date.issued2020-02-
dc.identifier.urihttps://repository.hanyang.ac.kr/handle/20.500.11754/123907-
dc.identifier.urihttp://hanyang.dcollection.net/common/orgView/200000436924en_US
dc.description.abstract디엘스-알더 반응은 가장 강력한 탄소-탄소 결합 형성 화학 반응 중 하나이며, conjugate 되어 있는 1,3-diene과 알켄 dienophile 사이에서 반응이 진행되어 cyclohexene 유도체를 생성합니다. 이로 인해, 많은 디엘스-알더 반응은 합성하기 어렵거나 흥미로운 생리활성을 띄는 천연물 합성을 위해 개발되고 성공적으로 적용이 되었다. 본 연구실에서는 이 디엘스-알더 반응을 다양한 천연물 합성과 그 천연물의 핵심 구조와 작용기들을 빠르게 만들기 위하여 3,5-dibromo-2-pyrone과 그 유도체를 새로운 1,3-diene으로 이용하여 개발하였다. 다양한 천연물 합성을 위한 노력의 일환으로, 최근 분자내 디엘스-알더 반응을 이용하여 천연물인 (+)-fusoxysporone-1, (-)-neocosmosin A, (+)-aplykurodinone-1 and (-)-cyanthiwigin F의 새로운 합성 방법을 계획하였다. 3,5-dibromo-2-pyrone의 3번 탄소 위치에 적절한 치환기가 달려 있는 적절한 dienophile을 도입하기 위해, 위치 선택적인 Sonogashira 커플링과 수은을 촉매로 이용한 hydration 반응을 이용하였다. 브롬화 알카인이 길게 달려있는 2-파이론의 분자내 디엘스-알더 반응은 (-)-neocosmosin A를 합성할 수 있는 거대 락톤 구조를 얻을 수 있었다. 그리고 분자내 수소 결합 이론을 기반으로 한 분자내 디엘스-알더 반응은 (+)-aplykurodinon-1의 합성에 도달할 수 있었다. 이러한 반응들을 적용하여 (+)-fusoxysporone-1과 (-)-cyanthowigin F의 합성을 연구하였다. | Diels-Alder reaction is one of the most powerful carbon-carbon bond forming chemical reactions, taking place between conjugated 1,3-diene and alkene dienophile to generate a substituted cyclohexene derivative. As such, many Diels-Alder reactions have been elaborated and successfully applied to the synthesis of the natural products with challenging chemical structures and/or intriguing biological activities. Our group has been developed 3,5-dibromo-2-pyrone and its derivatives as new 1,3-dienes for the rapid generation of core structures and functional groups embedded and thus needed for the synthesis of various natural products. As a part of the on-going efforts in our group, we recently designed new synthetic routes to (+)-fusoxysporone-1, (-)-neocosmosin A, (+)-aplykurodinone-1 and (-)-cyanthiwigin F by utilizing intramolecular Diels-Alder reactions (IMDA). Regioselective Sonogashira coupling and mercury-mediated hydration reactions allowed strategic incorporation of the dienophiles with the appropriate functional groups onto the C3 position of 3,5-dibromo-2-pyrone. IMDA of 2-pyrone with bromo-alkyne connected with a long tether proceeded quite nicely to afford macrolactone skeleton which was readily converted into (-)-neocosmosina A. Incorporation of internal hydrogen bonding concept allowed highly efficient π-facial selective IMDA reaction en route to the formal synthesis of (+)-aplykurodinone-1. Further applications of this method to (+)-fusoxysporone-1 and (-)-cyanthiwigin F are under progress.-
dc.description.abstractDiels-Alder reaction is one of the most powerful carbon-carbon bond forming chemical reactions, taking place between conjugated 1,3-diene and alkene dienophile to generate a substituted cyclohexene derivative. As such, many Diels-Alder reactions have been elaborated and successfully applied to the synthesis of the natural products with challenging chemical structures and/or intriguing biological activities. Our group has been developed 3,5-dibromo-2-pyrone and its derivatives as new 1,3-dienes for the rapid generation of core structures and functional groups embedded and thus needed for the synthesis of various natural products. As a part of the on-going efforts in our group, we recently designed new synthetic routes to (+)-fusoxysporone-1, (-)-neocosmosin A, (+)-aplykurodinone-1 and (-)-cyanthiwigin F by utilizing intramolecular Diels-Alder reactions (IMDA). Regioselective Sonogashira coupling and mercury-mediated hydration reactions allowed strategic incorporation of the dienophiles with the appropriate functional groups onto the C3 position of 3,5-dibromo-2-pyrone. IMDA of 2-pyrone with bromo-alkyne connected with a long tether proceeded quite nicely to afford macrolactone skeleton which was readily converted into (-)-neocosmosina A. Incorporation of internal hydrogen bonding concept allowed highly efficient π-facial selective IMDA reaction en route to the formal synthesis of (+)-aplykurodinone-1. Further applications of this method to (+)-fusoxysporone-1 and (-)-cyanthiwigin F are under progress.-
dc.publisher한양대학교-
dc.titleIntramolecular Diels-Alder reactions of 2-pyrones for the total synthesis of natural products-
dc.title.alternative파이론의 분자내 디엘스-알더 반응을 통한 천연물 전합성-
dc.typeTheses-
dc.contributor.googleauthorJoon-Ho Lee-
dc.contributor.alternativeauthor이준호-
dc.sector.campusS-
dc.sector.daehak대학원-
dc.sector.department화학과-
dc.description.degreeDoctor-
Appears in Collections:
GRADUATE SCHOOL[S](대학원) > THEATER & FILM(연극영화학과) > Theses (Ph.D.)
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE