The construction of the C/D ring system present in the diterpenoid alkaloids atisine and garryfoline

✍ Scribed by Russell A. Bell; Robert E. Ireland

• Publisher: Elsevier Science
• Year: 1963
• Tongue: French
• Weight: 243 KB
• Volume: 4
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90620-3

✦ Synopsis

One phase of any successful totally synthetic approach to the construction of the diterpenoid alkaloids atisine (l)l and garryfoline (2)1'2 must be the elaboration of the C/D bicyclic ring system. While a method for the construction of such ring systems would be premature without the availability of the necessary tetra-or pentacyclic substrates on which it could be applied, the recent successes of Edwards3 and Shlmizu4 In this latter endeavor suggests the value of reporting a C/D ring system synthesis at this time.

We recently reported5 the conversion of the unsaturated 1 For a recent review of the chemistry of these substances, see S. W. Pelletier, Tetrahedron l& 7 6 (1961).