Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B

Yuichi Momoi; Kei Ichiro Okuyama; Hiroki Toya; Kenji Sugimoto; Kentaro Okano; Hidetoshi Tokuyama

doi:10.1002/anie.201407686

Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B

Yuichi Momoi, Kei Ichiro Okuyama, Hiroki Toya, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

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

18 Citations (Scopus)

Abstract

The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía.

Original language	English
Pages (from-to)	13215-13219
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	48
DOIs	https://doi.org/10.1002/anie.201407686
Publication status	Published - 2014 Nov 24

Keywords

Alkaloids
Aromatic substitution
Cross-coupling
Cyclization
Total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201407686

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title = "Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B",

abstract = "The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zub{\'i}a.",

keywords = "Alkaloids, Aromatic substitution, Cross-coupling, Cyclization, Total synthesis",

author = "Yuichi Momoi and Okuyama, {Kei Ichiro} and Hiroki Toya and Kenji Sugimoto and Kentaro Okano and Hidetoshi Tokuyama",

note = "Publisher Copyright: {\textcopyright} 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

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T1 - Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B

AU - Momoi, Yuichi

AU - Okuyama, Kei Ichiro

AU - Toya, Hiroki

AU - Sugimoto, Kenji

AU - Okano, Kentaro

AU - Tokuyama, Hidetoshi

PY - 2014/11/24

Y1 - 2014/11/24

N2 - The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía.

AB - The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía.

KW - Alkaloids

KW - Aromatic substitution

KW - Cross-coupling

KW - Cyclization

KW - Total synthesis

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 48

ER -

Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B

Abstract

Keywords

ASJC Scopus subject areas

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