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-lactams
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3242-3249
- https://doi.org/10.1039/p19810003242
Abstract
4-Allylazetidin-2-one, prepared from penta-1,4-diene and chlorosulphonyl isocyanate, has been used to synthesise the parent 7-oxo-1-azabicyclo[3.2.0] hept-2-ene-2-carboxylate system of the naturally occurring olivanic acids, using an intramolecular Witting reaction to construct the 2,3-double bond. Cyclisation of ketones derived from the 4-allyl grouping produced 3-substituted derivatives, while use of the azetidin-2-one prepared from hexa-1,5-diene and chlorosulphonyl isocyanate has given the homologous 8-oxo-1-azabicyclo[4.2.0]oct-2-ene system.Keywords
This publication has 1 reference indexed in Scilit:
- C-19393 S2 and H2, new carbapenem antibiotics. II. Isolation and structures.The Journal of Antibiotics, 1980