Simultaneous accumulation of both skeletal and appendage-based diversities on tandem Ugi/Diels-Alder products

Masato Oikawa, Minoru Ikoma, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Diversity-oriented organic synthesis (DOS) is a key concept for construction of skeletally diverse small molecule libraries to discover drug-like small molecules. Here, we describe a DOS class to transform a complex 7-oxanorbornene skeleton, which is readily accessible by a tandem Ugi/Diels-Alder reaction, into two heterotricycle skeletons selectively by using tandem ROM/CM/RCM reaction. In the present study, the mode of cyclization is pre-encoded by building blocks used in the complexity-generating tandem Ugi/Diels-Alder reaction. Since variable alkenes can be used in the CM reaction, our approach can be extended to construct both skeleton- and appendage-diverse small molecule libraries.

Original languageEnglish
Pages (from-to)5863-5866
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number35
DOIs
Publication statusPublished - 2005 Aug 29

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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