Synthesis of the CDE/FG ring models of prymnesins

Reassignment of the relative configuration of the E/F ring juncture

Makoto Sasaki, Makoto Ebine, Hiroyuki Takagi, Hiroyuki Takakura, Takeshi Shida, Masayuki Satake, Yasukatsu Oshima, Tomoji Igarashi, Takeshi Yasumoto

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Synthesis of two diastereomeric models (3a and 3b) corresponding to the CDE/FG ring of prymnesins, polycyclic ether toxins isolated from the red tide phytoflagellate Prymnesium parvum, is described. Comparison of the 1H and 13C NMR data for each compound with those reported for prymnesins suggests that the earlier stereochemical assignment of the E/F ring juncture needs to be revised.

Original languageEnglish
Pages (from-to)1501-1504
Number of pages4
JournalOrganic Letters
Volume6
Issue number9
DOIs
Publication statusPublished - Apr 29 2004

Fingerprint

red tide
Haptophyta
rings
Tides
synthesis
configurations
Ether
ethers
Nuclear magnetic resonance
nuclear magnetic resonance
prymnesin
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
Gymnodinium breve toxin

All Science Journal Classification (ASJC) codes

  • Molecular Medicine

Cite this

Sasaki, M., Ebine, M., Takagi, H., Takakura, H., Shida, T., Satake, M., ... Yasumoto, T. (2004). Synthesis of the CDE/FG ring models of prymnesins: Reassignment of the relative configuration of the E/F ring juncture. Organic Letters, 6(9), 1501-1504. https://doi.org/10.1021/ol049569l

Synthesis of the CDE/FG ring models of prymnesins : Reassignment of the relative configuration of the E/F ring juncture. / Sasaki, Makoto; Ebine, Makoto; Takagi, Hiroyuki; Takakura, Hiroyuki; Shida, Takeshi; Satake, Masayuki; Oshima, Yasukatsu; Igarashi, Tomoji; Yasumoto, Takeshi.

In: Organic Letters, Vol. 6, No. 9, 29.04.2004, p. 1501-1504.

Research output: Contribution to journalArticle

Sasaki, M, Ebine, M, Takagi, H, Takakura, H, Shida, T, Satake, M, Oshima, Y, Igarashi, T & Yasumoto, T 2004, 'Synthesis of the CDE/FG ring models of prymnesins: Reassignment of the relative configuration of the E/F ring juncture', Organic Letters, vol. 6, no. 9, pp. 1501-1504. https://doi.org/10.1021/ol049569l
Sasaki, Makoto ; Ebine, Makoto ; Takagi, Hiroyuki ; Takakura, Hiroyuki ; Shida, Takeshi ; Satake, Masayuki ; Oshima, Yasukatsu ; Igarashi, Tomoji ; Yasumoto, Takeshi. / Synthesis of the CDE/FG ring models of prymnesins : Reassignment of the relative configuration of the E/F ring juncture. In: Organic Letters. 2004 ; Vol. 6, No. 9. pp. 1501-1504.
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