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Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4+3] Cycloaddition/SmI2-Pinacol Coupling
- Hassan, Ahmed H. E.;
- Lee, Jae Kyun;
- Pae, Ae Nim;
- Min, Sun-Joon;
- Cho, Yong Seo
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35초록
A synthetic approach toward the tricyclic 5,7,6-membered ring structure Of daphnane-family natural products is described. An intramolecular [4 + 3] cycloaddition reaction of furan with an oxypentadienyl cation constructed the oxa-bridged bicyclic structure in a stereoselective fashion. Structural analysis revealed that the desired exo isomer was predominantly acquired through epimerization. Finally, formation of the five-membered ring was achieved through SmI2-mediated pinacol coupling.
키워드
SYNAPTOLEPIS-KIRKII; 1ST SYNTHESIS; LATENT HIV; RESINIFERATOXIN; TIGLIANE; DITERPENES; CYCLOADDITIONS; CONSTRUCTION; PROSTRATIN; PHORBOL; 1ST SYNTHESIS; TIGLIANE; RESINIFERATOXIN; CYCLOADDITIONS; CONSTRUCTION; PROSTRATIN; DITERPENES; ANALOGS; PHORBOL; POTENT
- 제목
- Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4+3] Cycloaddition/SmI2-Pinacol Coupling
- 저자
- Hassan, Ahmed H. E.; Lee, Jae Kyun; Pae, Ae Nim; Min, Sun-Joon; Cho, Yong Seo
- 발행일
- 2015-06
- 유형
- Article
- 저널명
- Organic Letters
- 권
- 17
- 호
- 11
- 페이지
- 2672 ~ 2675
- 언어
- ENG
- 출판사
- AMER CHEMICAL SOC
- 발행국가
- 미국
- 분량
- 4 페이지
- ISSN
- E 1523-7052
P 1523-7060