title: Synthetic study of 1,3-butadiene-based IMDA approach to construct a [5-7-6] tricyclic core and its application to the total synthesis of C8-epi-guanacastepene O.
abstract: An efficient intramolecular Diels-Alder (IMDA) strategy for the construction of the [5-7-6] tricyclic core (18) of guanacastepenes has been developed from cis- and trans-1,3-butadiene-tethered 4-oxopent-2-ynoic acid ethyl esters 10 and 11. This method facilitates the synthesis of C8-epi-guanacastepene O (36) in a very efficient manner.
authors.affiliation: Key Laboratory of Bioorganic Chemistry and Molecular Engineering , Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Shenzhen Graduate School, Peking University, Beijing 100871, China.
authors.forename: Chuang-Chuang
authors.initials: CC
authors.lastname: Li
authors.forename: Cui-Hua
authors.initials: CH
authors.lastname: Wang
authors.forename: Bo
authors.initials: B
authors.lastname: Liang
authors.forename: Xin-Hao
authors.initials: XH
authors.lastname: Zhang
authors.forename: Lu-Jiang
authors.initials: LJ
authors.lastname: Deng
authors.forename: Shuang
authors.initials: S
authors.lastname: Liang
authors.forename: Jia-Hua
authors.initials: JH
authors.lastname: Chen
authors.forename: Yun-Dong
authors.initials: YD
authors.lastname: Wu
authors.forename: Zhen
authors.initials: Z
authors.lastname: Yang
mesh_terms: D002070:Butadienes / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D002070:Butadienes; D004224:Diterpenes; D007659:Ketones; C409194:guanacastepene; C031763:1,3-butadiene