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

研究成果: Article査読

1 被引用数 (Scopus)

抄録

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.

本文言語English
論文番号131197
ジャーナルTetrahedron
76
20
DOI
出版ステータスPublished - 2020 5 15

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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