4
views
0
recommends
+1 Recommend
0 collections
    0
    shares
      • Record: found
      • Abstract: found
      • Article: not found

      Total Synthesis and Structure Revision of (-)-Siphonodictyal B and Its Biomimetic Conversion into (+)-Liphagal.

      Read this article at

      ScienceOpenPublisherPubMed
      Bookmark
          There is no author summary for this article yet. Authors can add summaries to their articles on ScienceOpen to make them more accessible to a non-specialist audience.

          Abstract

          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.

          Related collections

          Author and article information

          Journal
          Org. Lett.
          Organic letters
          American Chemical Society (ACS)
          1523-7052
          1523-7052
          Sep 04 2015
          : 17
          : 17
          Affiliations
          [1 ] Department of Chemistry, University of Adelaide , Adelaide, SA 5005, Australia.
          Article
          10.1021/acs.orglett.5b01973
          26295981
          6fdd2a8c-0b85-449c-9c9d-b7851fcaf2a8
          History

          Comments

          Comment on this article