Abstract
Chiral secondary mixed alkylcopper-zinc reagents were prepared from the corresponding alkyl iodides and reacted with allylic epoxides via an anti -S (N) 2 '-substitution and retention of configuration of the chiral alkylorganometallic, leading to chiral allylic alcohols. This method was used in a total synthesis of the natural product (3 S ,6 R ,7 S )-zingiberenol in 8 steps and 9.7% overall yield [dr (3 S ,6 R ) = 99:1;dr (6 R ,7 S ) = 81:19] starting from commercially available 3-methyl-2-cyclohexenone.
Item Type: | Journal article |
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Faculties: | Chemistry and Pharmacy > Department of Chemistry |
Subjects: | 500 Science > 540 Chemistry |
ISSN: | 0039-7881 |
Language: | English |
Item ID: | 90018 |
Date Deposited: | 25. Jan 2022 09:33 |
Last Modified: | 25. Jan 2022 09:33 |