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Synthesis of (+)-(4S, 8R)hyphen;8hyphen;Epi- and (−)-(4R, 8S)-4-Epi-β-bisabolol

✍ Scribed by Georg Fráter; Urs Müller

Publisher
John Wiley and Sons
Year
1989
Tongue
German
Weight
347 KB
Volume
72
Category
Article
ISSN
0018-019X

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✦ Synopsis

The first total enantioselective synthesis of (+)-(4S,8R)-8-epi-~-bisabolol((+)-l) and of (-)-(4R,SS)-4-epi-Bhisaholol ((-)-1) is reported. The key step in the synthesis is the kinetic resolution of (&)-5 by means of the Shurpless epoxidation yielding (-)-and (+)-6, respectively. Reduction of the epoxides with LiAIH, gave the diols (+)and (-)-7 which were transformed into (+)-and (-)-8, respectively, via the corresponding mesylate. Reaction of these epoxides with the Grignard reagent derived from homoprenylbromide, assisted by Li,CuCI,, finished the synthesis of the target compounds 1 with high diastereo-and enantioselectivity.

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