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Synthese yon 2,6-Diencarbonsäuren Vorläufige Mitteilung

✍ Scribed by György Fráter

Publisher
John Wiley and Sons
Year
1975
Tongue
German
Weight
479 KB
Volume
58
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Through sequential Claisen‐ and Cope rearrangements the chainlengthening of allylic alcohols by one isoprene unit was achieved. Treatment of (E)‐1a first with lithium N‐cyclohexyl‐N‐isopropylamide at −70°, followed by trimethylsilylchloride and warming up to room temperature yielded after work‐up 3a (R = H), which rearranged at 156° in high yield to (E/Z)‐4a. An analogous reaction sequence transformed 6 to 8. Choosing lithium N‐methylanilide as a base (E/Z)‐9 was selectively rearranged to 12, which was converted to the Cecropia juvenile hormone precursor (E/Z)‐4b.

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