The intramolecular Diels-Alder strategy

Applications to total synthesis of natural products

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

Research output: Contribution to journalArticle

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
Publication statusPublished - 2002 Jul
Externally publishedYes

Fingerprint

Stereoselectivity
Regioselectivity
Cycloaddition
Biological Products
Derivatives
Organic Chemistry
cyclohexene

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

The intramolecular Diels-Alder strategy : Applications to total synthesis of natural products. / Suzuki, Yoshikazu; Murata, Takeshi; Takao, Kenichi; Tadano, Kin Ichi.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 60, No. 7, 07.2002, p. 679-690.

Research output: Contribution to journalArticle

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