Radical macrocyclisations in synthesis. A new approach to mukulol and marine cembranolide lactones
β Scribed by Nicholas J.G Cox; Gerald Pattenden; Stuart D Mills
- Publisher
- Elsevier Science
- Year
- 1989
- Tongue
- French
- Weight
- 251 KB
- Volume
- 30
- Category
- Article
- ISSN
- 0040-4039
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A new entry into pyrroloiminoquinone marine alkaloids, makaluvamines, has been developed. The key 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline intermediates 11 and 18 were laepared by atyne-mediated cyclization of the 4-chloro-6-methoxytryptamine derivatives 10 and 17, respectively. The requisite s
## Abstract The thiolactone oxime 10 was synthesized in ten steps from the known triβ__O__βbenzylglucose 13, which was transformed into the oxime 14, silylated (β 15), and mesylated (β 16). Treatment of 16 with Bu~4~NF yielded the Lβ__ido__βepoxide 17 and the hydroxylamine 18; the isomeric Dβ__gluc