Exploring an expedient IMDA reaction approach to construct the guanacastepene core.
Construction of the [5-7-6] tricyclic core of guanacastepenes was attempted by using the intramolecular Diels-Alder (IMDA) reaction and Me(3)Al-mediated ring opening of the oxabridge as key synthetic steps. The illustrated chemistry demonstrated a synthetic feasibility to build up the framework of guanacastepenes by the IMDA reaction. [reaction: see text]
Li
Chuang-Chuang
CC
Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education, College of Chemistry, State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, Beijing 100871, China.
Liang
Shuang
S
Zhang
Xin-Hao
XH
Xie
Zhi-Xiang
ZX
Chen
Jia-Hua
JH
Wu
Yun-Dong
YD
Yang
Zhen
Z
D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
D004224:Diterpenes; C409194:guanacastepene