Hassan, Ahmed H. E. Lee, Jae Kyun Pae, Ae Nim Min, Sun-Joon Cho, Yong Seo 2024-01-20T07:00:43Z 2024-01-20T07:00:43Z 2021-09-05 2015-06-05 1523-7060 https://pubs.kist.re.kr/handle/201004/125336 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. English AMER CHEMICAL SOC 1ST SYNTHESIS TIGLIANE RESINIFERATOXIN CYCLOADDITIONS CONSTRUCTION PROSTRATIN DITERPENES ANALOGS PHORBOL POTENT Synthesis of the Tricyclic Ring Structure of Daphnanes via Intramolecular [4+3] Cycloaddition/SmI2-Pinacol Coupling Article 10.1021/acs.orglett.5b01054 1 ORGANIC LETTERS, v.17, no.11, pp.2672 - 2675 ORGANIC LETTERS 17 11 2672 2675 scie scopus 000355962200028 2-s2.0-84930959767 Chemistry, Organic Chemistry Article 1ST SYNTHESIS TIGLIANE RESINIFERATOXIN CYCLOADDITIONS CONSTRUCTION PROSTRATIN DITERPENES ANALOGS PHORBOL POTENT daphnanes Pinacol coupling [4+3] cycloaddition