Total Synthesis of 3-epi-Juruenolide C

Noriki Kutsumura; Mai Inagaki; Akito Kiriseko; Takao Saito

doi:10.1248/cpb.c19-00209

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Total Synthesis of 3-epi-Juruenolide C

Noriki Kutsumura , Mai Inagaki, Akito Kiriseko, Takao Saito

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Keywords: total synthesis, 3-epi-juruenolide C, γ-lactone, one-pot regioselective bromination, intramolecular carbonylation, face-selective hydrogenation

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Supplementary material

2019 Volume 67 Issue 6 Pages 594-598

DOI https://doi.org/10.1248/cpb.c19-00209

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Abstract

In this study, the total synthesis of 3-epi-juruenolide C is achieved in 10 steps (longest linear sequence) starting from ethyl (2E,4S,5S)-4,5-dihydroxy-2-hexenoate. The synthetic highlights of our approach include one-pot regioselective bromination, intramolecular carbonylation using bis(triphenylphosphine)dicarbonylnickel, and face-selective hydrogenation using a homogeneous Wilkinson’s catalyst.

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