Further studies on CAB approach toward chemical conversion of C19-diterpenoid alkaloids to taxoids: synthesis of the vital intermediate C-nor-aconanone.

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-C19 bonds in 11 or 21 by treatment with m-CPBA and subsequently with LTA, as well as the rupture of the N-C17 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.

• Authors: Xiang-Li Shen, Qiao-Hong Chen, Feng-Peng Wang
• Journal: Journal of Asian natural products research (J Asian Nat Prod Res) Vol. 11 Issue 2 Pg. 97-109 ( 2009) ISSN: 1477-2213 [Electronic] England
• PMID: 19219720 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Alkaloids
• Diterpenes
• Drugs, Chinese Herbal
• Taxoids

Topics

• Alkaloids (chemical synthesis, chemistry)
• Diterpenes (chemical synthesis, chemistry)
• Drugs, Chinese Herbal (chemical synthesis, chemistry)
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Taxoids (chemical synthesis, chemistry)