Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (1)

Takahiro Suzuki, Natsumi Tanaka, Takehiko Matsumura, Yosuke Hosoya, Masahisa Nakada

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Construction of the ABCD ring system of (-)-FR182877 via the highly diastereoselective intramolecular Diels-Alder (IMDA) reaction is described. The IMDA reaction of the α,β-unsaturated aldehyde generated in situ from the corresponding acetal successfully provided the desired product 14 possessing the AB ring system as the single diastereomer. The CD ring system was constructed by the subsequent IMHDA reaction and the additional experiment suggested that the diastereoselectivity of the IMHDA reaction could be related to the E/Z geometry of alkene 17, which was generated in situ from 16.

Original languageEnglish
Pages (from-to)6483-6487
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number37
DOIs
Publication statusPublished - 2007 Sep 10

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthetic studies on (-)-FR182877: construction of the ABCD ring system via the intramolecular cycloadditions (1)'. Together they form a unique fingerprint.

  • Cite this