The lactone 2 was found to be a co-product of the BF etherate induced cyclization of epoxyisogermacrone 2. The ketal 3 when treated with 100% HCOOH afforded the lactone 5-while underthe same condltlons the ketol 4 gave the corresponding ester 5. A mechanism is suggested for the rearrangements. Rece
Modification of the Skeleton of Homoharringtonine through Unusual Rearrangements
โ Scribed by Takano, Ichiro; Yasuda, Ichiro; Nishijima, Motohiro; Hitotsuyanagi, Yukio; Takeya, Koichi; Itokawa, Hideji
- Book ID
- 126952738
- Publisher
- American Chemical Society
- Year
- 1997
- Tongue
- English
- Weight
- 137 KB
- Volume
- 62
- Category
- Article
- ISSN
- 0022-3263
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๐ SIMILAR VOLUMES
## Latifolin (Id) Is an important memter of the neoflavanoia group of -pwa6. AS recently descriteal its synthesis Involves an ionic coupling of trlmethoxy benzene tc,) and o-methoxy clnnamyl ceticn CC9>, the latter being generated from o-methoxp clnnamyl chloride by a Lewis acid.
The addition of an acetyl radical on caryophyllene leads to formation of the four isomeric ketones 5-8 involving a novel rearrangement of the caryophyllene skeleton. The acid catalyzed rearrangement of caryophyllene 1 has been studied in detail'. The final re-\_ action products are clovene 2, caryo