Loading...
Please wait, while we are loading the content...
Similar Documents
Synthesis of Chiral 3′-Hydroxy-γ-ionylideneacetic Acids
| Content Provider | Scilit |
|---|---|
| Author | Yamamoto, Hiroshi Oritani, Takayuki Yamashita, Kyohei |
| Copyright Year | 1988 |
| Description | Journal: Bioscience, Biotechnology, and Biochemistry Four isomers of chiral 3′-hydroxy-γ-ionylideneacetic acid (3′-hydroxy-γ-acid), acidic metabolites of Cercospora cruenta, were synthesized from (+)-(S)-3-hydroxy-2,2-dimethyl-1-cyclohexa-none as the chiral starting material. A [2.3]-sigmatropic rearrangement of (+)-(S)-3,3-dimethyl-4-tetrahydropyranyloxy-1-cyclohexenemethanol, which was followed by two steps of the Wittig reaction, gave (+)-(1′S,3′S)-(2E,4E)-and (+)-(1′S,3′S)-(2Z,4E)-3′-hydroxy-γ-acids. Oxidation and subsequent reduction of (+)-(1′S,3′S)-(2E,4E)-3′-hydroxy-γ-acid methyl ester gave (−)-(1′S,3′R)-(2E,4E)-ester, which was isomerized to (−)-(1′S,3′R)-(2Z,4E)-ester by ultra violet irradiation. |
| Related Links | https://www.tandfonline.com/doi/pdf/10.1080/00021369.1988.10869011?needAccess=true |
| Ending Page | 2208 |
| Page Count | 6 |
| Starting Page | 2203 |
| ISSN | 09168451 |
| e-ISSN | 13476947 |
| DOI | 10.1080/00021369.1988.10869011 |
| Journal | Bioscience, Biotechnology, and Biochemistry |
| Issue Number | 9 |
| Volume Number | 52 |
| Language | English |
| Publisher | Informa UK Limited |
| Publisher Date | 1988-09-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: Bioscience, Biotechnology, and Biochemistry Organic Chemistry Ionylideneacetic Acid Γ Ionylideneacetic |
| Content Type | Text |
| Subject | Organic Chemistry Medicine Analytical Chemistry Molecular Biology Biochemistry Applied Microbiology and Biotechnology Biotechnology |
