Asymmetric Total Synthesis of Epolactaene.

• Marumoto Shinji

  Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd.

• Kogen Hiroshi

  Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd.

Bibliographic Information

Other Title

• エポラクタエンの不斉全合成
• エポラクタエン ノ フセイ ゼンゴウセイ

Abstract

A total synthesis of the neuritegenic agent, epolactaene has been achieved via a convergent approach in 14 steps from optically active lactaldehyde derivatives. The key steps include (i) the stereoselective aldol reaction between malonate ester enolate and α-alkoxy aldehyde (ii) diastereospecific lactonization of malonate ester (iii) E-selective Wittig reaction. The optical rotation was identical with that of the natural (+) -epolactaene, which establishes that the absolute configuration of natural (+) -epolactaene is (13R, 14R) definitively. Other several epoxy-γ-lactam compounds also synthesized which suggest this method would be general for organic synthesis.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 58 (3), 183-191, 2000

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• total synthesis
• epolactaene
• neurotrophic factor
• malonate ester
• stereoselective aldol reaction
• epoxylactone
• E-selective Wittig reaction
• epoxylactam

Details

• CRID: 1390282680254816384
• NII Article ID: 10008819273
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.58.183
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 5301703
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I5301703
• Text Lang: ja
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed