Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereoselective synthesis of iridoid natural products.
[reaction: see text] Iridoid natural products 1-4 are accessed stereoselectively by means of tridentate (Schiff base)Cr(III)-catalyzed hetero-Diels-Alder reactions between ethyl vinyl ether and enantioenriched 5-methyl-1-cyclopentene-1-carboxaldehyde. An efficient route to the aldehyde from citronellal is afforded by the ring-closing metathesis reaction.
Chavez
David E
DE
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Jacobsen
Eric N
EN
D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D004583:Electrons; D013237:Stereoisomerism
D001688:Biological Products