(±)-6-epi-goniothalesdiol과 (±)-parvistone E의 입체선택적 전합성
Stereoselective total synthesis of (±)-6-epi-goniothalesdiol A and (±)-parvistone E
- 주제(키워드) trans-2-Aryl-6-alkyl tetrahydropyran (THP) , 6-epi-Goniothalesdiol A , Parvistone E , Intramolecular oxidative cycloetherification , Diastereoselective
- 발행기관 아주대학교
- 지도교수 이동주
- 발행년도 2019
- 학위수여년월 2019. 2
- 학위명 석사
- 학과 및 전공 일반대학원 약학과
- 실제URI http://www.dcollection.net/handler/ajou/000000028866
- 본문언어 영어
- 저작권 아주대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
Stereoselective total synthesis of trans-2-aryl-6-alkyl tetrahydropyran (THP) natural products (±)-6-epi-goniothalesdiol A (3) and (±)-parvistone E (2) has been achieved from the readily available allylic alcohol (±)-8 in 8 and 9 steps in overall yield of 20.9% and 9.4%, respectively. A direct intramolecular oxidative cycloetherification reaction of (E)-1-aryl-5-hydroxyalkene (±)-7 promoted by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as an oxidant proceeds via a 6-endo-trig pathway cleanly to construct the rare and challenging trans-2-aryl-6-alkyl-3,4-dihydropyran framework (±)-6 in 70% yield and with good diastereoselectivity (trans/cis = 75:25).
more목차
I. Introduction 1
II. Results and Discussions 3
III. Conclusion 8
IV. Experimentals 9
1. Materials and Methods 9
2. Experimental Procedures 10
V. References 17
VI. Appendix 19
VII. Abstracts in Korean 21
