Total synthesis of (+)-trans-195A.
[reaction: see text] The first enantioselective synthesis of (+)-trans-195A is described. The structure has been constructed by ring-rearrangement metathesis (RRM) and zirconium-mediated Negishi-coupling, used for the first time to prepare 6,6-membered heterocycles, as key steps. By comparison of the synthesized material with the isolated natural product, the absolute configuration of natural trans-195A was determined to be (2R,4aS,5R,8aS)-(-).
Holub
Nicole
N
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 135, D-10623 Berlin, Germany.
Neidhöfer
Jürgen
J
Blechert
Siegfried
S
D000470:Alkaloids / Q000737:chemistry; D000818:Animals; D001001:Anura / Q000378:metabolism; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C506845:195A compound; D000470:Alkaloids; D001688:Biological Products; D007202:Indicators and Reagents; D011804:Quinolines; C011093:pumiliotoxin C