Total Synthesis of (±)-Kopsihainanine A

• Published in: Chemistry : a European journal Vol. 18; no. 22; pp. 6729 - 6732
• Main Authors: Jing, Peng, Yang, Zhen, Zhao, Changgui, Zheng, Huaiji, Fang, Bowen, Xie, Xingang, She, Xuegong
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 29.05.2012; WILEY‐VCH Verlag; Wiley
• Subjects: alkaloids; Chemistry; Chemistry, Multidisciplinary; Heterocyclic Compounds, 4 or More Rings - chemical synthesis; Heterocyclic Compounds, 4 or More Rings - chemistry; indoles; intramolecular conjugate addition; kopsihainanine A; Molecular Structure; oxidation; Oxidation-Reduction; Physical Sciences; Science & Technology; Stereoisomerism; total synthesis; kopsihainanine A; ENANTIOSELECTIVE SYNTHESIS; alkaloids; oxidation; QUATERNARY CARBON CENTERS; INTRAMOLECULAR RITTER REACTION; indoles; total synthesis; INDOLE ALKALOIDS; CORE STRUCTURE; AMINOCYCLOPROPANES; intramolecular conjugate addition; CYCLIZATION

Going all the way: The first total synthesis of (±)‐kopsihainanine A has been achieved in ten steps with a 12 % overall yield from commercially available 1,2,3,4‐tetrahydrocarbazol‐4‐one (see scheme). This synthesis features an intramolecular conjugate addition of the iminium ion formed in situ with...