Synthetic studies on bacilosarcins a and b, and related natural products

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3 Citations (Scopus)

Abstract

The first total synthesis of two herbicidal natural products bacilosarcins A and B, the former of which incorporates a totally unprecedented heterobicyclic ring system and the latter contains a very rare heterecyclic structural motif, has been accomplished. The irregular ring systems in bacilosarcins A and B were constructed in very simple manners by means of an Amadori-type /V-alkylation reaction as well as by taking advantage of the thermodynamic stability of the targeted rings. The total synthesis of PM-94128 and Y-05460 M-A, cytotoxic natural products of microbial origin, has also been accomplished by a concise nine-step sequence from L-leucine and L-valine, respectively. The first synthesis of Y-05460 M-A enabled its stereochemical determination.

Original languageEnglish
Pages (from-to)387-398
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume68
Issue number4
DOIs
Publication statusPublished - 2010 Apr 1

Keywords

  • Amadori rearrangement
  • Amicoumacin
  • Bacilosarcin
  • Epoxide ring opening
  • Heterocycles
  • Hydro-xylactonization
  • Isocoumarin
  • Stereoconvergent cyclization
  • Tautomerization

ASJC Scopus subject areas

  • Organic Chemistry

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