Synthesis of Two Macrocyclic Fragments of Manadomanzamine Alkaloids

Yuki Kurihara; Atsushi Azuma; Haruka Yasufuku; Shinsaku Takikawa; Noritaka Chida; Takaaki Sato

doi:10.1246/cl.220452

Synthesis of Two Macrocyclic Fragments of Manadomanzamine Alkaloids

Yuki Kurihara, Atsushi Azuma, Haruka Yasufuku, Shinsaku Takikawa, Noritaka Chida, Takaaki Sato

Department of Applied Chemistry

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

Abstract

The synthesis of two macrocyclic fragments in the manadomanzamine alkaloids based on a strategy using reductive nucleophilic addition to macrolactams is reported. The sequence through the Wittig coupling and macrolactamization gives quick access to both eleven-membered and ten-membered macrolactams. The iridium-catalyzed reductive Strecker reaction of the ten-membered macrolactam takes place via the corresponding unstable imine intermediate.

Original language	English
Pages (from-to)	1146-1149
Number of pages	4
Journal	Chemistry Letters
Volume	51
Issue number	12
DOIs	https://doi.org/10.1246/cl.220452
Publication status	Published - 2022 Dec

Keywords

Amide
Manzamine alkaloid
Total synthesis

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.220452

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title = "Synthesis of Two Macrocyclic Fragments of Manadomanzamine Alkaloids",

abstract = "The synthesis of two macrocyclic fragments in the manadomanzamine alkaloids based on a strategy using reductive nucleophilic addition to macrolactams is reported. The sequence through the Wittig coupling and macrolactamization gives quick access to both eleven-membered and ten-membered macrolactams. The iridium-catalyzed reductive Strecker reaction of the ten-membered macrolactam takes place via the corresponding unstable imine intermediate.",

keywords = "Amide, Manzamine alkaloid, Total synthesis",

author = "Yuki Kurihara and Atsushi Azuma and Haruka Yasufuku and Shinsaku Takikawa and Noritaka Chida and Takaaki Sato",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research (B) from MEXT (22H02084). Publisher Copyright: {\textcopyright} 2021 The Chemical Society of Japan.",

year = "2022",

month = dec,

doi = "10.1246/cl.220452",

language = "English",

volume = "51",

pages = "1146--1149",

journal = "Chemistry Letters",

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T1 - Synthesis of Two Macrocyclic Fragments of Manadomanzamine Alkaloids

AU - Kurihara, Yuki

AU - Azuma, Atsushi

AU - Yasufuku, Haruka

AU - Takikawa, Shinsaku

AU - Chida, Noritaka

AU - Sato, Takaaki

PY - 2022/12

Y1 - 2022/12

N2 - The synthesis of two macrocyclic fragments in the manadomanzamine alkaloids based on a strategy using reductive nucleophilic addition to macrolactams is reported. The sequence through the Wittig coupling and macrolactamization gives quick access to both eleven-membered and ten-membered macrolactams. The iridium-catalyzed reductive Strecker reaction of the ten-membered macrolactam takes place via the corresponding unstable imine intermediate.

AB - The synthesis of two macrocyclic fragments in the manadomanzamine alkaloids based on a strategy using reductive nucleophilic addition to macrolactams is reported. The sequence through the Wittig coupling and macrolactamization gives quick access to both eleven-membered and ten-membered macrolactams. The iridium-catalyzed reductive Strecker reaction of the ten-membered macrolactam takes place via the corresponding unstable imine intermediate.

KW - Amide

KW - Manzamine alkaloid

KW - Total synthesis

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SP - 1146

EP - 1149

JO - Chemistry Letters

JF - Chemistry Letters

IS - 12

ER -

Synthesis of Two Macrocyclic Fragments of Manadomanzamine Alkaloids

Abstract

Keywords

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