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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. 11(2)
- 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.
- Subjects :
- Stereochemistry
Imine
Pharmaceutical Science
Cleavage (embryo)
Chemical synthesis
Analytical Chemistry
Semipinacol rearrangement
chemistry.chemical_compound
Polycyclic compound
Alkaloids
Drug Discovery
Nuclear Magnetic Resonance, Biomolecular
Pharmacology
chemistry.chemical_classification
Molecular Structure
Chemistry
Organic Chemistry
General Medicine
Nef reaction
Complementary and alternative medicine
Molecular Medicine
Taxoids
Diterpene
Diterpenes
Lactone
Drugs, Chinese Herbal
Subjects
Details
- ISSN :
- 14772213
- Volume :
- 11
- Issue :
- 2
- Database :
- OpenAIRE
- Journal :
- Journal of Asian natural products research
- Accession number :
- edsair.doi.dedup.....e3337c3f99a16703f740fcc8391c8096