Determination of the absolute structure of (+)-akaterpin

Hayato Hosoi; Nobuyuki Kawai; Hideki Hagiwara; Takahiro Suzuki; Atsuo Nakazaki; Ken Ichi Takao; Kazuo Umezaw; Susumu Kobayashi

doi:10.1248/cpb.60.137

Determination of the absolute structure of (+)-akaterpin

Hayato Hosoi, Nobuyuki Kawai, Hideki Hagiwara, Takahiro Suzuki, Atsuo Nakazaki, Ken Ichi Takao, Kazuo Umezaw, Susumu Kobayashi

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

2 Citations (Scopus)

Abstract

We describe the total synthesis and structural determination of (+)-akaterpin (1), an inhibitor of phosphatidylinositol- specific phospholipase C (PI-PLC). The key features of the synthetic strategy include the resolution of β,γ-unsaturated ketone (±)-2a with chiral sulfoximine 6. The absolute stereochemistry was determined by comparison of the specific optical rotation data of (+)-1 and (-)-1 with that of natural akaterpin.

Original language	English
Pages (from-to)	137-143
Number of pages	7
Journal	Chemical and Pharmaceutical Bulletin
Volume	60
Issue number	1
DOIs	https://doi.org/10.1248/cpb.60.137
Publication status	Published - 2012 Jan
Externally published	Yes

Keywords

Absolute stereochemistry
Optical resolution
Total synthesis

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.60.137

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keywords = "Absolute stereochemistry, Optical resolution, Total synthesis",

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AU - Hosoi, Hayato

AU - Kawai, Nobuyuki

AU - Hagiwara, Hideki

AU - Suzuki, Takahiro

AU - Nakazaki, Atsuo

AU - Takao, Ken Ichi

AU - Umezaw, Kazuo

AU - Kobayashi, Susumu

PY - 2012/1

Y1 - 2012/1

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AB - We describe the total synthesis and structural determination of (+)-akaterpin (1), an inhibitor of phosphatidylinositol- specific phospholipase C (PI-PLC). The key features of the synthetic strategy include the resolution of β,γ-unsaturated ketone (±)-2a with chiral sulfoximine 6. The absolute stereochemistry was determined by comparison of the specific optical rotation data of (+)-1 and (-)-1 with that of natural akaterpin.

KW - Absolute stereochemistry

KW - Optical resolution

KW - Total synthesis

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Determination of the absolute structure of (+)-akaterpin

Abstract

Keywords

ASJC Scopus subject areas

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