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.
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.
Li
Chuang-Chuang
CC
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.
Wang
Cui-Hua
CH
Liang
Bo
B
Zhang
Xin-Hao
XH
Deng
Lu-Jiang
LJ
Liang
Shuang
S
Chen
Jia-Hua
JH
Wu
Yun-Dong
YD
Yang
Zhen
Z
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
D002070:Butadienes; D004224:Diterpenes; D007659:Ketones; C409194:guanacastepene; C031763:1,3-butadiene