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

doi:10.1021/ol049569l

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

LIF - Molecular and Chemical Life Science

Research output: Contribution to journal › Article › peer-review

26 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 language	English
Pages (from-to)	1501-1504
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	9
DOIs	https://doi.org/10.1021/ol049569l
Publication status	Published - 2004 Apr 29

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10.1021/ol049569l

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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.",

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

year = "2004",

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doi = "10.1021/ol049569l",

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T1 - Synthesis of the CDE/FG ring models of prymnesins

T2 - Reassignment of the relative configuration of the E/F ring juncture

AU - Sasaki, Makoto

AU - Ebine, Makoto

AU - Takagi, Hiroyuki

AU - Takakura, Hiroyuki

AU - Shida, Takeshi

AU - Satake, Masayuki

AU - Oshima, Yasukatsu

AU - Igarashi, Tomoji

AU - Yasumoto, Takeshi

PY - 2004/4/29

Y1 - 2004/4/29

N2 - 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.

AB - 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.

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Synthesis of the CDE/FG ring models of prymnesins: Reassignment of the relative configuration of the E/F ring juncture

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