Total synthesis of 20-norsalvinorin A. 1. Preparation of a key intermediate.
The key tricyclic intermediate 3a, for the total synthesis of the C(20)-nor analogue of salvinorin A, was prepared in seven steps from 3-furaldehyde. Key steps involved a highly regio- and diastereoselective Lewis acid assisted Diels-Alder reaction followed by base-promoted epimerization and a completely stereoselective conjugate reduction.
Bergman
Ylva E
YE
School of Chemistry, Monash University, PO Box 23, Victoria 3800, Australia.
Mulder
Roger
R
Perlmutter
Patrick
P
D045785:Diterpenes, Clerodane / Q000138:chemical synthesis*; D005662:Furaldehyde / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D013237:Stereoisomerism
D045785:Diterpenes, Clerodane; D006575:Heterocyclic Compounds, 3-Ring; D005662:Furaldehyde; C090499:salvinorin A