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Further studies on CAB approach toward chemical conversion of C19-diterpenoid alkaloids to taxoids: synthesis of the vital intermediate C-nor-aconanone.
- Source :
-
Journal of Asian Natural Products Research . Feb2009, Vol. 11 Issue 2, p97-109. 13p. 4 Diagrams, 1 Chart. - Publication Year :
- 2009
-
Abstract
- In the title study, the synthesis of the vital intermediate C-nor-aconanone (3) from 4 was completed through 11 steps, mainly including semipinacol rearrangement, formation of the imines by the treatment of 10 or 20 with NBS, the cleavage of N-C(19) bonds in 11 or 21 by treatment with m-CPBA and subsequently with LTA, as well as the rupture of the N-C(17) bonds in 22 by a modified Nef reaction (NaH/t-BuOH → KMnO4/H2O). One-pot procedure was successfully developed starting from 11 or 21 to afford the N,19-seco-C-nor product 15 or 22, respectively, in reasonably good yields. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ALKALOIDS
*HYDROXYL group
*HYDROLYSIS
*KETONES
*THERAPEUTICS
*NITROGEN
Subjects
Details
- Language :
- English
- ISSN :
- 10286020
- Volume :
- 11
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Journal of Asian Natural Products Research
- Publication Type :
- Academic Journal
- Accession number :
- 36504625
- Full Text :
- https://doi.org/10.1080/10286020801967128