Studies toward the Total Synthesis of Nominine
- 21 November 2007
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (26) , 10130-10140
- https://doi.org/10.1021/jo701995u
Abstract
The construction of the hetisane group of alkaloids, of which the extensively bridged nominine 17 is the simplest member, poses the ultimate challenge for those interested in the synthesis of the C20 diterpene alkaloids. We describe the synthesis of an advanced intermediate toward this goal. The key steps include reductive acylation, reductive deoxygenation, Birch reduction, and an intramolecular Lewis acid-catalyzed 1,6-addition of a carbamate to a dienone.Keywords
This publication has 13 references indexed in Scilit:
- Efficient Synthetic Access to the Hetisine C20-Diterpenoid Alkaloids. A Concise Synthesis of Nominine via Oxidoisoquinolinium-1,3-Dipolar and Dienamine-Diels−Alder CycloadditionsJournal of the American Chemical Society, 2006
- Total Synthesis of (±)‐Nominine, a Heptacyclic Hetisine‐Type Aconite AlkaloidAngewandte Chemie International Edition in English, 2004
- The effects of Aconitum alkaloids on the central nervous systemPublished by Elsevier ,1998
- Regioselective synthesis of β-ketoesters from lithium enolates and methyl cyanoformateTetrahedron Letters, 1983
- Proton NMR studies of 15N-labeled Escherichia coli tRNAfMet. Use of 1J1H-15N couplings to identify imino resonances of uridine-related basesJournal of the American Chemical Society, 1982
- Biogenetic-type total synthesis of (.+-.)-triptonide and (.+-.)-triptolideJournal of the American Chemical Society, 1982
- Chemistry of organosilicon compounds. 99. Conjugate addition of allylsilanes to .alpha.,.beta.-enones. A New method of stereoselective introduction of the angular allyl group in fused cyclic .alpha.,.beta.-enonesJournal of the American Chemical Society, 1977
- The Total Synthesis of Racemic NapellineCanadian Journal of Chemistry, 1974
- Stereoselective total synthesis of (+-)-eremoligenol, (+-)-eremophilene, (+-) ,-valerianol, and (+-)-valenceneThe Journal of Organic Chemistry, 1970
- Synthesis of Some Resin AcidsJournal of the American Chemical Society, 1964