Total Synthesis and Absolute Stereochemistry of Seragakinone A

DOI

Bibliographic Information

Other Title
  • 20 セラガキノンAの全合成(口頭発表の部)

Abstract

Serakakinone A (1), an antifungal and antibacterial compound, was produced by an unidentified marine fungus symbiotic to rhodophyta Ceratodictyon spongiosum collected at Seragaki beach, Okinawa. The intriguing structure of 1 features a densely oxygenated pentacyclic structure with angular prenylation, as determined by extensive spectroscopic studies and single-crystal X-ray analysis, although the absolute configuration remained unassigned. Three major challenges in planning a symthetic route are: (1) the construction of the pentacyclic framework, (2) the stereoselective introduction of a prenyl unit into the sterically hindered angular position, and (3) the regio- and stereo-controlled installation of multiple oxygen functionalities. In this talk, we will present the first asymmetric total synthesis of (-)-seragakinone A. Noteworthy features of the synthesis include: (1) the benzoin-forming reactions worked well at two cyclization stages, including one catalytic enantioselective reaction, (2) the pinacol-type rearrangement was effective for installing tghe angular prenyl substituent. The synthetic material was identical in all respects to the natural sample, except for the sign of optical rotation, thereby allowing the assignment of the synthetic material as the antipode of the natural product.

Journal

Details 詳細情報について

  • CRID
    1390001206077619072
  • NII Article ID
    110009757744
  • DOI
    10.24496/tennenyuki.52.0_115
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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