Structures of spiroindicumides A and B, unprecedented carbon skeletal spirolactones, and determination of the absolute configuration by vibrational circular dichroism exciton approach

Teigo Asai, Tohru Taniguchi, Takashi Yamamoto, Kenji Monde, Yoshiteru Oshima

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

Spiroindicumides A (1) and B (2), novel spirolactone polyketides, were isolated from a filamentous fungus, Chaetomium indicum, cultivated in the presence of a histone deacetylase inhibitor. Their structures including relative configurations were determined by spectroscopic analyses. Their absolute configurations were unambiguously assigned by the vibrational circular dichroism (VCD) exciton chirality method using only ca. 0.3 mg of each sample. This study presents the first application of the VCD exciton approach to novel natural products. A possible biosynthetic pathway of the new compounds was also proposed.

Original languageEnglish
Pages (from-to)4320-4323
Number of pages4
JournalOrganic letters
Volume15
Issue number17
DOIs
Publication statusPublished - 2013 Sep 6

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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