| Autor: |
Markwell-Heys AW; Department of Chemistry, University of Adelaide , Adelaide, SA 5005, Australia., Kuan KK; Department of Chemistry, University of Adelaide , Adelaide, SA 5005, Australia., George JH; Department of Chemistry, University of Adelaide , Adelaide, SA 5005, Australia. |
| Jazyk: |
angličtina |
| Zdroj: |
Organic letters [Org Lett] 2015 Sep 04; Vol. 17 (17), pp. 4228-31. Date of Electronic Publication: 2015 Aug 21. |
| DOI: |
10.1021/acs.orglett.5b01973 |
| Abstrakt: |
The structure of siphonodictyal B has been reassigned on the basis of the total synthesis of both possible C-8 epimers. The revised structure of siphonodictyal B was converted into liphagal by acid catalyzed rearrangement of a proposed epoxide intermediate. This biomimetic cascade features a succession of four distinct reactions (epoxidation, o-quinone methide formation, ring expansion, and benzofuran formation) that occur in a one-pot operation under mild conditions. During these studies we also isolated a surprisingly stable o-quinone methide that supports our mechanistic proposal for liphagal biosynthesis. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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