Efficient entry into 2-substituted tetrahydroquinoline systems through alkylative ring expansion: stereoselective formal synthesis of (+/-)-martinellic acid.
A new efficient synthesis of 2-substituted tetrahydroquinolines has been achieved by the domino reaction of N-indanyl(methoxy)amines, which consists of three types of reactions: elimination of an alcohol, the rearrangement of an aryl group, and the addition of an organolithium or magnesium reagent. The synthetic utility of this approach is demonstrated by the stereoselective formal synthesis of (+/-)- martinellic acid.
Ueda
Masafumi
M
Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Kawai
Sayuri
S
Hayashi
Masataka
M
Naito
Takeaki
T
Miyata
Okiko
O
D000478:Alkylation; D002384:Catalysis; D008094:Lithium / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009942:Organometallic Compounds; D011758:Pyrroles; D011804:Quinolines; C432345:martinellic acid; D008094:Lithium; C542964:1,2,3,4-tetrahydroquinoline; D008274:Magnesium