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.

journal_name

J Asian Nat Prod Res

authors

Shen XL,Chen QH,Wang FP

doi

10.1080/10286020801967128

subject

Has Abstract

pub_date

2009-01-01 00:00:00

pages

97-109

issue

2

eissn

1028-6020

issn

1477-2213

pii

908712374

journal_volume

11

pub_type

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