Remarkable Diastereoselectivity Eserted by Dienophile Configuration in Intramolecular Diels-Alder Reaction of Electron Deficient Heterodienes: New Chiral Entry into the Secoiridoid Monoterpenes and the Heteroyohibine Indole Alkaloids
- 1 January 1990
- journal article
- research article
- Published by CLOCKSS Archive in HETEROCYCLES
- Vol. 30 (1) , 583-605
- https://doi.org/10.3987/com-89-s70
Abstract
Reaction between the optically active glyceraldehyde (1Z) carrying Z-olefin and Meldrum''s acid furnished in one step the tricyclic adduct 3 with trans 5/6 ring juncture selectively under mild conditions by spontaneous condensation followed by the intramolecular Diels-Alder reaction. On the other hand, the E-olefin isomer (1E), under the same conditions, furnished the isomeric adduct 4 with cis 5/6 ring juncture selectively. The former gave a pair of the cis-fused bicyclic carbamates, (22) and (25), while the latter gave the trans-fused pair, (23) and (26), by the following transformations. Although these imply formal chiral route to the heteroyohimbine alkaloids, a new enantioselective route to a secoiridoid monoterpene, (-)-methyl elenolate (37), has also been developed.Keywords
This publication has 1 reference indexed in Scilit:
- Enantioselective synthesis of (-)-kainic acidJournal of the American Chemical Society, 1988