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A Convergent Approach to Cyclopeptide Alkaloids: Total Synthesis of Sanjoinine G1

✍ Scribed by Temal-Laïb, Taoues; Chastanet, Jacqueline; Zhu, Jieping

Book ID
121387444
Publisher
American Chemical Society
Year
2002
Tongue
English
Weight
126 KB
Volume
124
Category
Article
ISSN
0002-7863

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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 (

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Macrocylization via formation of aryl-alkyl ether bond was a key step in a model synthesis of 14-membered cyclopeptide alkaloids. A new chemoenzymadc synthesis of chiral 2amino-l-arylethanol was developed in the course of this study