Catalyst-Controlled Inverse-Electron-Demand Hetero-Diels−Alder Reactions in the Enantio- and Diastereoselective Synthesis of Iridoid Natural Products
- 6 June 2003
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (14) , 2563-2565
- https://doi.org/10.1021/ol034883l
Abstract
[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.Keywords
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