The intramolecular Diels-Alder strategy: Applications to total synthesis of natural products

Yoshikazu Suzuki, Takeshi Murata, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalReview articlepeer-review

18 Citations (Scopus)

Abstract

The Diels-Alder reaction is one of the most valuable reactions in synthetic organic chemistry. This [4 + 2] cycloaddition produces a cyclohexene derivative with concomitant generation of up to four new stereogenic centers. Particularly, intramolecular version has attracted many organic chemists due to forming polycyclic skeleton with high regio- and stereoselectivity under mild conditions. Thus, the intramolecular Diels-Alder reaction has shown its broad utility for the construction of various complex ring systems. In this review, we summarize the regio-, endo/exo, and/or π-facial selective intramolecular Diels-Alder reactions of type I for total synthesis of natural products, which have been published in recent years.

Original languageEnglish
Pages (from-to)679-690
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume60
Issue number7
DOIs
Publication statusPublished - 2002 Jul
Externally publishedYes

Keywords

  • Endo/exo selectivity
  • Intramolecular Diels-Alder reaction
  • Natural product synthesis
  • Regioselectivity
  • Total synthesis
  • Type I triene
  • π-facial selectivity

ASJC Scopus subject areas

  • Organic Chemistry

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