Olivanic acid analogues. Part 4. Cycloaddition reactions of p-nitrobenzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, and synthesis of the 8-oxo-1-azatricyclo[4.2.0.02,4]octane-2-carboxylate system
- 31 December 1985
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 973-981
- https://doi.org/10.1039/p19860000973
Abstract
p-Nitrobenzyl 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1) participated in Diels–Alder and 1,3-dipolar cycloaddition reactions, yielding a range of novel polycyclic azetidinone structures. The two 8-oxo-1-azatricyclo [4.2.0.02,4]octane-2-carboxylates (21) and (24) were prepared, and their cyclopropane stereochemistries assigned using nuclear Overhauser difference spectroscopy. Sodium (1′RS,2SR,4RS,6RS,7SR)-7-(1-hydroxyethyl)-8-oxo-l-azatricyclo[4.2.0.0.2,4]octane-2-carboxylate (37) was synthesised from compound (1)via p-nitrobenzyl (1′RS,5RS,6SR)-6-[1-(p-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (32).This publication has 3 references indexed in Scilit:
- Olivanic acid analogues. Part 2. Total synthesis of some C(6)-substituted 7-oxo-1 -azabicyclo[3.2.0] hept-2-ene-2-carboxylatesJournal of the Chemical Society, Perkin Transactions 1, 1985
- Olivanic acid analogues. Part 3. Total synthesis of C(6α)-methoxy-substituted 7-oxo-1 -azabicyclo[3.2.0] hept-2-ene-2-carboxylatesJournal of the Chemical Society, Perkin Transactions 1, 1985
- Olivanic acid analogues. Part 1. Total synthesis of the 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate system and some related β-lactamsJournal of the Chemical Society, Perkin Transactions 1, 1981