✦ LIBER ✦
Use of the electrophilic c-arylation by aryllead triacetates in the construction of synthons for aizoaceae and amaryllidaceae alkaloid synthesis
✍ Scribed by Darren J. Ackland; John T. Pinhey
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 201 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
The vinylogous 8-keto esters, ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate (Hagemann's Ester) (4), ethyl 4-oxocyclohex-l-enecarboxylate (7a) and its double bond isomer (7b), undergo regiospecific arylation with aryllead triacetates at Cl; reaction of the mixture of isomers ( 7a) and ( 7b) with aryllead compounds (5a), (5~) and (5d) provides intermediates for the synthesis of (+)-o-methyljoubertiamine
(1) , (f)-mesembrine ( 2) and (+)-lycoramine (3) respectively.