Total synthesis of (-)-8-deoxyserratinine via an efficient Helquist annulation and double N-alkylation reaction.
The first enantioselective total synthesis of (-)-8-deoxyserratinine has been achieved in 15 steps from enone 4 with 7% overall yield. The key features include a highly efficient Helquist annulation to furnish the cis-fused 6/5 bicycle, facile construction of the aza nine-membered ring system employing double N-alkylation strategy, as well as asymmetric Shi epoxidation, delivering the desired beta-epoxide stereospecifically.
Yang
Yu-Rong
YR
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650204, China. yangyurong@mail.kib.ac.cn
Lai
Zeng-Wei
ZW
Shen
Liang
L
Huang
Jiu-Zhong
JZ
Wu
Xing-De
XD
Yin
Jun-Lin
JL
Wei
Kun
K
D000478:Alkylation; D004852:Epoxy Compounds / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C553068:8-deoxyserratinine; D004852:Epoxy Compounds; D007212:Indolizines