Enantioselective total synthesis of (-)-flustramines A, B and (-)-flustramides A, B via domino olefination/isomerization/Claisen rearrangement sequence.
The concise total synthesis of marine alkaloids, (-)-flustramines A and B, and (-)-flustramides A and B has been achieved through the domino olefination/isomerization/Claisen rearrangement (OIC) for highly enantioselective construction of the asymmetric quaternary carbon center and the chemoselective reduction-cyclization (RC) for pyrrolidine formation as key steps.
Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo, 204-8588, Japan. kawasaki@my-pharm.ac.jp
Tomomi
T
Kawasaki
Masahi
M
Shinada
Daigo
D
Kamimura
Mayu
M
Ohzono
Atsuyo
A
Ogawa
D000470:Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D007536:Isomerism; D008956:Models, Chemical; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D026121:Indole Alkaloids; D011759:Pyrrolidines; C519054:flustramide A; C519053:flustramide B; C041253:flustramine A; C041254:flustramine B; C032519:pyrrolidine