Synthetic Studies toward Dimeric Indole Alkaloids Based on Convergent Synthetic Strategy

Research output: Contribution to journalReview article

Abstract

The total syntheses of dimeric indole alkaloids, haplophytine, and T988s are described. These dimeric compounds comprising two structurally different indole units are ubiquitous in nature, and many possess pharmaceutically important activities. To realize an efficient chemical synthesis of these dimeric indole alkaloids, the establishment of convergent synthetic strategies and development of new coupling methods are indispensable. The linkage of two highly functionalized units at a late stage of the synthesis frequently induces synthetic problems such as chemoselectivity and steric repulsion. Moreover, although transition metal-catalyzed reactions are usually an effective method for the cross-coupling of two units, the application of these cross-coupling reactions to bond formation involving a sterically hindered C(sp3) is often difficult. Thus, even with precise modern synthetic methods, it is currently difficult to realize convergent syntheses of dimeric indole alkaloids possessing a quaternary carbon linking two units. To combat these synthetic problems, we developed a synthetic method to link two indole units using an Ag-mediated nucleophilic substitution reaction. In this review, we provide a detailed discussion of convergent synthetic strategies and coupling methods for dimeric indole alkaloids.

Original languageEnglish
Pages (from-to)117-128
Number of pages12
JournalChemical & pharmaceutical bulletin
Volume68
Issue number2
DOIs
Publication statusPublished - 2020 Jan 1

Keywords

  • chemoselectivity
  • convergent synthesis
  • coupling reaction
  • dimeric indole alkaloid
  • silver bis(trifluoromethanesulfonyl)imide
  • total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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