DFT supported structural elucidations of seiridiasteriscane A, unique 15-nor-asteriscane and novel pestalotiopsin Congeners from Seiridium sp. KT3957

Wilanfranco C. Tayone, Mami Nishiyama, Kazuaki Tanaka, Maeda Hayato, Masaru Enomoto, Masaru Hashimoto

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Seiridiasteriscane A (1), pestalotiopsins L-N (2–4), and 2-O-deacetylpestalotiopsin A (5) were isolated along with known pestalotiopsins A (7), B (6), and fuscoatrol A (8) from Seiridium sp. KT3957. Their relative structures were elucidated by extensive NMR analysis and verified using DFT (density functional theory) chemical shift calculations. The absolute configurations were determined by reproducing their experimental ECD spectra based on DFT calculations. Although 3 and 4 existed as conformational mixtures in CDCl3, DFT-based 13C chemical shift calculations were useful for evaluating each conformer. Simultaneous isolation of seiridiasteriscane A (1) and pestalotiopsins 2–8 suggested a plausible route for the biosynthesis of 1 involving the expansion of the cyclobutane moiety into a cyclopentane ring.

Original languageEnglish
Article number131197
JournalTetrahedron
Volume76
Issue number20
DOIs
Publication statusPublished - 2020 May 15

Keywords

  • Chemical shift calculations
  • ECD spectral Calculations
  • Pestalotiopsins L-N
  • Seiridiasteriscane A
  • Seiridium sp. KT3957

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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