Synthetic Approach toward the Structural Elucidation of Symbiodinolide: Stereodivergent Synthesis and Stereostructural Revision of the C79-C104 Fragment

• Takamura Hiroyoshi

  Graduate School of Natural Science and Technology, Okayama University

Bibliographic Information

Other Title

• シンビオジノライドの構造解明に向けた合成化学的アプローチ：C79-C104フラグメントの立体発散的合成と立体構造改訂
• シンビオジノライド ノ コウゾウ カイメイ ニ ムケタ ゴウセイ カガクテキ アプローチ : C79-C104 フラグメント ノ リッタイ ハッサンテキ ゴウセイ ト リッタイ コウゾウ カイテイ

Abstract

Stereoselective synthesis of the proposed C79-C104 fragment of symbiodinolide, a polyol marine natural product, revealed that the stereochemistry of the C91-C99 carbon chain domain of this natural product needs to be reassigned. Next, stereodivergent synthesis of eight possible diastereomers corresponding to the C79-C97 and C94-C104 fragments resulted in the proposal of two candidate stereostructures, respectively. The synthesis of four candidate compounds of the C79-C104 fragment and comparison of their ¹³C NMR data with those of the natural product allowed stereostructural revision of this fragment of symbiodinolide.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 76 (5), 474-477, 2018-05-01

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• natural product
• polyol
• stereochemistry
• stereodivergent synthesis
• stereoselective synthesis
• structural elucidation
• symbiodinolide
• synthetic approach

Details

• CRID: 1390001205339219584
• NII Article ID: 130006733908
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.76.474
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 029057652
• Web Site: http://id.ndl.go.jp/bib/029057652
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I029057652
• Web Site: https://www.jstage.jst.go.jp/article/yukigoseikyokaishi/76/5/76_474/_pdf
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed