Enantioselective Synthesis of the Spirotetracyclic Carbon Core of Mangicols by Using a Stereoselective Transannnnular Diels-Alder Strategy

Keisuke Araki, Keiji Saito, Hirokazu Arimoto, Daisuke Uemura

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

"TADA!" is not the trumpet fanfare but the transannular Diels-Alder reaction concluding the synthesis of the tetracyclic core of the mangicols, a family of marine sesterterpenes. Further highlights in the synthesis include a novel chlorination and an intramolecular Nozaki-Hiyama-Kishi coupling reaction. Bn=benzyl.

Original languageEnglish
Pages (from-to)81-84
Number of pages4
JournalAngewandte Chemie - International Edition
Volume43
Issue number1
DOIs
Publication statusPublished - 2004 Dec 22
Externally publishedYes

Keywords

  • Cycloaddition
  • Diastereoselectivity
  • Natural products
  • Spiro compounds
  • Synthesis design

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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