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Transformation of artemisin into artapshin and 8α-hydroxy-11β,13-dihydrobalchanin

✍ Scribed by Isabel Fernández; Begoña García; Jose R. Pedro


Book ID
104205087
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
496 KB
Volume
43
Category
Article
ISSN
0040-4020

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✦ Synopsis


Rbstract: Partial syntheses of the -86squiterpeni lactones artapshin (1) and 8g-hydroxy-jlB,13-dihydrobiilchanin (21 f ram qrtemisin (2) are described.


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A seven-step synthesis of a new intermediate (5a,fa,llfi)-3,6dioxogermacr-l-cn-l3,7-olide (10) is describcd starting from [ -)-~-santonin (I). The key stcp in thc transformation was photolytic skclctal rearrangement of (4qSP,601,11 F)-S-hydroxy-2oxoeudesman-l3.6-olide (9) to the W e compound, scnsit