Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration

Yujiro Kitamura; Hiroyuki Koshino; Takemichi Nakamura; Aya Tsuchida; Teruhiko Nitoda; Hiroshi Kanzaki; Koji Matsuoka; Shunya Takahashi

doi:10.1016/j.tetlet.2013.01.015

Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration

Yujiro Kitamura, Hiroyuki Koshino, Takemichi Nakamura, Aya Tsuchida, Teruhiko Nitoda, Hiroshi Kanzaki, Koji Matsuoka, Shunya Takahashi

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

21 Citations (Scopus)

Abstract

Pochonicine is a polyhydroxylated pyrrolizidine alkaloid with a powerful inhibitory activity against β-Nacetylglucosaminidases. The proposed structure for pochonicine and the three diastereomers concerning its C-1 and/or C-3 positions were synthesized from N-acetyl-D-glucosamine through construction of the pyrrolizidine skeleton by two intramolecular amino cyclizations as key steps. This synthetic study not only revised the structure of the natural product to the corresponding 1,3-di-epi-form but also determined the absolute configuration as 1R, 3S, 5R, 6R, 7S, 7aR.

Original language	English
Pages (from-to)	1456-1459
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	11
DOIs	https://doi.org/10.1016/j.tetlet.2013.01.015
Publication status	Published - Mar 13 2013

Keywords

D-Allopyranoside
GlcNAcase inhibitor
N-Acetyl-D-glucosamine
Pochonicine

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.01.015

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title = "Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration",

abstract = "Pochonicine is a polyhydroxylated pyrrolizidine alkaloid with a powerful inhibitory activity against β-Nacetylglucosaminidases. The proposed structure for pochonicine and the three diastereomers concerning its C-1 and/or C-3 positions were synthesized from N-acetyl-D-glucosamine through construction of the pyrrolizidine skeleton by two intramolecular amino cyclizations as key steps. This synthetic study not only revised the structure of the natural product to the corresponding 1,3-di-epi-form but also determined the absolute configuration as 1R, 3S, 5R, 6R, 7S, 7aR.",

keywords = "D-Allopyranoside, GlcNAcase inhibitor, N-Acetyl-D-glucosamine, Pochonicine",

author = "Yujiro Kitamura and Hiroyuki Koshino and Takemichi Nakamura and Aya Tsuchida and Teruhiko Nitoda and Hiroshi Kanzaki and Koji Matsuoka and Shunya Takahashi",

note = "Funding Information: This work was supported by the Chemical Genomics Project (RIKEN) and in part by the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT, No. 24580168 ). ",

year = "2013",

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day = "13",

doi = "10.1016/j.tetlet.2013.01.015",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration

AU - Kitamura, Yujiro

AU - Koshino, Hiroyuki

AU - Nakamura, Takemichi

AU - Tsuchida, Aya

AU - Nitoda, Teruhiko

AU - Kanzaki, Hiroshi

AU - Matsuoka, Koji

AU - Takahashi, Shunya

N1 - Funding Information: This work was supported by the Chemical Genomics Project (RIKEN) and in part by the Ministry of Education, Culture, Sports, Science and Technology of Japan (MEXT, No. 24580168 ).

PY - 2013/3/13

Y1 - 2013/3/13

N2 - Pochonicine is a polyhydroxylated pyrrolizidine alkaloid with a powerful inhibitory activity against β-Nacetylglucosaminidases. The proposed structure for pochonicine and the three diastereomers concerning its C-1 and/or C-3 positions were synthesized from N-acetyl-D-glucosamine through construction of the pyrrolizidine skeleton by two intramolecular amino cyclizations as key steps. This synthetic study not only revised the structure of the natural product to the corresponding 1,3-di-epi-form but also determined the absolute configuration as 1R, 3S, 5R, 6R, 7S, 7aR.

AB - Pochonicine is a polyhydroxylated pyrrolizidine alkaloid with a powerful inhibitory activity against β-Nacetylglucosaminidases. The proposed structure for pochonicine and the three diastereomers concerning its C-1 and/or C-3 positions were synthesized from N-acetyl-D-glucosamine through construction of the pyrrolizidine skeleton by two intramolecular amino cyclizations as key steps. This synthetic study not only revised the structure of the natural product to the corresponding 1,3-di-epi-form but also determined the absolute configuration as 1R, 3S, 5R, 6R, 7S, 7aR.

KW - D-Allopyranoside

KW - GlcNAcase inhibitor

KW - N-Acetyl-D-glucosamine

KW - Pochonicine

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U2 - 10.1016/j.tetlet.2013.01.015

DO - 10.1016/j.tetlet.2013.01.015

M3 - Article

AN - SCOPUS:84874940207

SN - 0040-4039

VL - 54

SP - 1456

EP - 1459

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Total synthesis of the proposed structure for pochonicine and determination of its absolute configuration

Abstract

Keywords

ASJC Scopus subject areas

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