Determination of the absolute structure of (+)-akaterpin

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)137-143
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume60
Issue number1
DOIs
Publication statusPublished - 2012 Jan
Externally publishedYes

Fingerprint

Optical rotation
Phosphoinositide Phospholipase C
Optical Rotation
Stereochemistry
Ketones
akaterpin

Keywords

  • Absolute stereochemistry
  • Optical resolution
  • Total synthesis

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Hosoi, H., Kawai, N., Hagiwara, H., Suzuki, T., Nakazaki, A., Takao, K., ... Kobayashi, S. (2012). Determination of the absolute structure of (+)-akaterpin. Chemical and Pharmaceutical Bulletin, 60(1), 137-143. https://doi.org/10.1248/cpb.60.137

Determination of the absolute structure of (+)-akaterpin. / Hosoi, Hayato; Kawai, Nobuyuki; Hagiwara, Hideki; Suzuki, Takahiro; Nakazaki, Atsuo; Takao, Kenichi; Umezaw, Kazuo; Kobayashi, Susumu.

In: Chemical and Pharmaceutical Bulletin, Vol. 60, No. 1, 01.2012, p. 137-143.

Research output: Contribution to journalArticle

Hosoi, H, Kawai, N, Hagiwara, H, Suzuki, T, Nakazaki, A, Takao, K, Umezaw, K & Kobayashi, S 2012, 'Determination of the absolute structure of (+)-akaterpin', Chemical and Pharmaceutical Bulletin, vol. 60, no. 1, pp. 137-143. https://doi.org/10.1248/cpb.60.137
Hosoi, Hayato ; Kawai, Nobuyuki ; Hagiwara, Hideki ; Suzuki, Takahiro ; Nakazaki, Atsuo ; Takao, Kenichi ; Umezaw, Kazuo ; Kobayashi, Susumu. / Determination of the absolute structure of (+)-akaterpin. In: Chemical and Pharmaceutical Bulletin. 2012 ; Vol. 60, No. 1. pp. 137-143.
@article{fc998536ed624404ad085e87af4c8fa6,
title = "Determination of the absolute structure of (+)-akaterpin",
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.",
keywords = "Absolute stereochemistry, Optical resolution, Total synthesis",
author = "Hayato Hosoi and Nobuyuki Kawai and Hideki Hagiwara and Takahiro Suzuki and Atsuo Nakazaki and Kenichi Takao and Kazuo Umezaw and Susumu Kobayashi",
year = "2012",
month = "1",
doi = "10.1248/cpb.60.137",
language = "English",
volume = "60",
pages = "137--143",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "1",

}

TY - JOUR

T1 - Determination of the absolute structure of (+)-akaterpin

AU - Hosoi, Hayato

AU - Kawai, Nobuyuki

AU - Hagiwara, Hideki

AU - Suzuki, Takahiro

AU - Nakazaki, Atsuo

AU - Takao, Kenichi

AU - Umezaw, Kazuo

AU - Kobayashi, Susumu

PY - 2012/1

Y1 - 2012/1

N2 - 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.

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

UR - http://www.scopus.com/inward/record.url?scp=84862931137&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84862931137&partnerID=8YFLogxK

U2 - 10.1248/cpb.60.137

DO - 10.1248/cpb.60.137

M3 - Article

VL - 60

SP - 137

EP - 143

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 1

ER -