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A facile synthesis of the 20-hydroxyecdysone side chain via a dihydrofuran derivative

✍ Scribed by Udo Hedtmann; Peter Welzel

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
118 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Key steps of a new synthesis of the ZO-hydroxyecdysone side chain are (i) addition of 2 to ZO-ketopregnanes and (ii) the stereoselective reduction of the 22-keto group after OH group protection. PO-Hydroxyecdysone (IZb) plays a major regulatory role during the postembryonic development of insects and ill the crustacean molting cycle.' One of the most challenging aspects of the synthesis of this important hormone2 Is the stereocontrolled construction of the side chain 3 With its two centers of chirality. We detail in this communication a highly convergent and stereospecific solution to this problem. Our strategy is centered around the use of 2 as C 22-C27 fragment. Coupling of 2 with a 20-oxopregnane such as 8a or 8b provides in In a single operation the complete carbon framework of 12. Lithlatlon of 2,2-dimethyl-2,3-dlhydrofuran4

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