The enantioselective total synthesis of nemotin.
The allene-diyne natural product nemotin was synthesized for the first time through an enantioselective route with the stereogenic center at the lactone moiety derived from l-glutamic acid and the allene axis constructed from the corresponding propargylic tosylate, and the absolute configuration was thus established as (4S,5aS).
Jian
Ya-Jun
YJ
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
Wu
Yikang
Y
D000466:Alkadienes / Q000138:chemical synthesis*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D018698:Glutamic Acid / Q000737:chemistry*; D051664:Kv1.3 Potassium Channel; D007783:Lactones / Q000737:chemistry*; D008956:Models, Chemical; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000466:Alkadienes; D000972:Antineoplastic Agents, Phytogenic; D051664:Kv1.3 Potassium Channel; D007783:Lactones; D012724:Sex Attractants; D018698:Glutamic Acid; C025947:propadiene