Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (−)-Goniomitine, (+)-Aspidospermidine, and (−)-Quebrachamine

Beau P. Pritchett, Jun Kikuchi, Yoshitaka Numajiri, Brian M. Stoltz

研究成果: Article査読

46 被引用数 (Scopus)

抄録

The successful application of dihydropyrido[1,2-a]indolone (DHPI) substrates in Pd-catalyzed asymmetric allylic alkylation chemistry facilitates rapid access to multiple alkaloid frameworks in an enantioselective fashion. Strategic bromination at the indole C3 position greatly improved the allylic alkylation chemistry and enabled a highly efficient Negishi cross-coupling downstream. The first catalytic enantioselective total synthesis of (−)-goniomitine, along with divergent formal syntheses of (+)-aspidospermidine and (−)-quebrachamine, are reported herein.

本文言語English
ページ(範囲)13529-13532
ページ数4
ジャーナルAngewandte Chemie - International Edition
55
43
DOI
出版ステータスPublished - 2016 10月 17
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)

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「Enantioselective Pd-Catalyzed Allylic Alkylation Reactions of Dihydropyrido[1,2-a]indolone Substrates: Efficient Syntheses of (−)-Goniomitine, (+)-Aspidospermidine, and (−)-Quebrachamine」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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