ChemInform Abstract: Total Synthesis of the Cyclopeptide Alkaloid Sanjoinine G1 and Its C-11 Epimer.

✍ Scribed by S. P. EAST; F. SHAO; L. WILLIAMS; M. M. JOULLIE

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199911248

✦ Synopsis

Total Synthesis of the Cyclopeptide Alkaloid Sanjoinine G1 and Its C-11 Epimer.

-An efficient new synthesis (18 steps, 6.6% overall yield) of sanjoinine G1 (VIII) is reported. The key steps in this synthesis are the formation of the alkyl-aryl ether linkage via an S N Ar reaction of amino alcohol (II) with nitrile (III) and the macrolactamization of precursor (V) to provide the C-OH epimers (VI) and (VII) using a modification of Schmidt's procedure. Treatment of epimer (VII) under the same conditions as (VI) gives the corresponding C-11 epimer of sanjoinine G1. -(EAST, S.