Total Synthesis of DL-Isoretronecanol and DL-Trachelanthamidine using Anodic Methoxylation in a Key Functionalizing Step.
- 1 January 1984
- journal article
- research article
- Published by Danish Chemical Society in Acta Chemica Scandinavica
- Vol. 38b (4) , 297-302
- https://doi.org/10.3891/acta.chem.scand.38b-0297
Abstract
The title substances were synthesized in 6 steps from simple starting materials. The key step involved anodic functionalization of the tertiary amide 9 followed by an intramolecular amidoalkylation, thus creating the pyrrolizidine ring system in 11. The 2 diastereomeric pairs of compounds 4a and 4b were then separated by column chromatography. These lactams were reduced cleanly with retained stereochemistry to the title subtances 1a and 1b, respectively. An attempt at an intramolecular amidoalkylation of the monoester 3 resulted in the formation of an 0-alkylated product, the ketene acetal 6.This publication has 3 references indexed in Scilit:
- Electroorganic chemistry. 60. Electroorganic synthesis of enamides and enecarbamates and their utilization in organic synthesisJournal of the American Chemical Society, 1982
- New approaches to the pyrrolizidine ring system: total synthesis of (.+-.)-isoretronecanol and (.+-.)-trachelanthamidineThe Journal of Organic Chemistry, 1978
- Recent Synthetic Methods Involving Intermolecular alpha;-Amidoalkylation at CarbonSynthesis, 1970