新奇遠隔不斉誘導反応によるポリアセテート型 およびアセテート─プロピオネート混合型 ポリケチドの合成

Seijiro Hosokawa*

*この研究の対応する著者

研究成果: Article査読

抄録

Polyacetate-type and acetate-propionate hybrid-type polyketide skeletons have been constructed by the remote asymmetric induction of the vinylogous Mukaiyama aldol reactions using chiral oxazolidinone-attached vinylketene silyl N,O-acetals. In the acetate-propionate hybrid-type reaction, anti- and syn-adducts were selectively afforded using aldehydes and acetals, respectively. Therefore, in conjunction with the previously reported polypropionate-type reaction, all types of polyketide skeletons have been able to be synthesized. In addition to the transition states of the acetate-propionate hybrid-type reactions, difference of the stereo-control systems between the polyacetate-type reaction and the polypropionate-type reaction is discussed. Interestingly, in polyacetate-type and acetate-propionate hybrid-type reactions, the chiral auxiliary controlled the stereoselectivity indirectly. Additionally, (S)-massoialactone (α,β-unsaturated δ-lactone) and tabtoxinine-β-lactam, an inhibitor of glutamate synthetase, were synthesized by the remote asymmetric induction reactions.

寄稿の翻訳タイトルSynthesis of poly acetate and acetate-propionate hybrid-type polyketides using novel remote asymmetric induction reactions
本文言語Japanese
ページ(範囲)109-119
ページ数11
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
79
2
DOI
出版ステータスPublished - 2021 2 1

Keywords

  • O-acetal
  • Polyacetate
  • Polyketide
  • Remote asymmetric induction
  • Stereodivergent synthesis
  • Vinylketene silyl N
  • Vinylogous Mukaiyama aldol reaction

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「新奇遠隔不斉誘導反応によるポリアセテート型 およびアセテート─プロピオネート混合型 ポリケチドの合成」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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