Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring

Yuko Izuchi; Hiroyuki Koshino; Yayoi Hongo; Nobuhiro Kanomata; Shunya Takahashi

doi:10.1021/ol2011117

Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring

Yuko Izuchi, Hiroyuki Koshino^*, Yayoi Hongo, Nobuhiro Kanomata, Shunya Takahashi

^*Corresponding author for this work

School of Advanced Science and Engineering

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

16 Citations (Scopus)

Abstract

Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.

Original language	English
Pages (from-to)	3360-3363
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	13
DOIs	https://doi.org/10.1021/ol2011117
Publication status	Published - 2011 Jul 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2011117

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abstract = "Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.",

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AU - Izuchi, Yuko

AU - Koshino, Hiroyuki

AU - Hongo, Yayoi

AU - Kanomata, Nobuhiro

AU - Takahashi, Shunya

PY - 2011/7/1

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Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring

Abstract

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