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Peracid induced oxidative rearrangements of triterpenoids: Products of new skeleton from bauerenyl acetate

✍ Scribed by Ajit Kumar Chakravarty; Binayak Das; Kazuo Masuda; Yoko Arai; Kenji Shiojima

Book ID
104208590
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
736 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

Treatment of bauerenyl acetate (2) with m-chloroperbenzoic acid at 4 Β°C yielded the migrated pcoducls, viz. 7c~-hyckoxy-14,27-cycloisoursan-3[l-yl acetate (9) ~d its 15Β’~-hy&oxy derivative (12) belonging to a new skeleton, 7a-hydroxyisours-14-en-3[$-yl acetate (10) and 14Β’t,15c~-epoxy-7ct-hydcox~3~-yl acetate (11), besides 7a,8ct-epoxytmueran-3~-yi acetate (3), baucxa-7,9(ll)-die~ 3[t-yl acetate (4), beucca-6,8-dien-31~yi acetate ($), 7~8a-epoxybauer-9(ll)-en-3~-yl aceta~ (6), 7a, Sa,9Β’~l lct-d~epoxybaueran-3~yl ace~e ( 7) and 8~9a-epoxy-7a-hy&oxybaueran-3~-yl acetsle (8). The $1~-~s of all the products were elt~l.,~l__ mainly on the basis of 2D NMR spectral mmlyses. The IH and 13C chemical shifts of bauea'enyi acetate (2) and its reaction products (3-12) were assigned unambiguonaly.

πŸ“œ SIMILAR VOLUMES

ChemInform Abstract: Peracid-Induced Oxi
ChemInform Abstract: Peracid-Induced Oxidative Rearrangements of Triterpenoids: Products of New Skeleton from Bauerenyl Acetate.
✍ A. K. CHAKRAVARTY; B. DAS; K. MASUDA; Y. ARAI; K. SHIOJIMA πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 40 KB πŸ‘ 2 views

The title reaction leads to the rearranged products (III)-(VI) in addition to the compounds (II) and (VII)-(XI). Derivatives (III) and (IV) possess a new 14,27-cycloisoursane skeleton and (V) and (VI) are isoursane derivatives. -(CHAKRAVARTY, A.