Scalable synthesis of the L/N ring of maitotoxin

Masashi Nakamura; Mizuki Jintoku; Hayato Kishigami; Yuki Kitayama; Taishin Taniguchi; Kohei Torikai; Yoko Yasuno; Masayuki Satake; Tohru Oishi

doi:10.1016/j.tetlet.2024.155221

Scalable synthesis of the L/N ring of maitotoxin

Masashi Nakamura, Mizuki Jintoku, Hayato Kishigami, Yuki Kitayama, Taishin Taniguchi, Kohei Torikai, Yoko Yasuno, Masayuki Satake, Tohru Oishi

Organic and Biological Chemistry

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

Abstract

A scalable method for synthesizing the L/N ring of maitotoxin corresponding to an unnatural L-glucose derivative was developed via the MacMillan method and C-glycosylation under flow conditions. The longest linear sequence from Z-2-buten-1,4-diol was 7 steps with 10 total steps.

Original language	English
Article number	155221
Journal	Tetrahedron Letters
Volume	147
DOIs	https://doi.org/10.1016/j.tetlet.2024.155221
Publication status	Published - Sept 1 2024

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2024.155221

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title = "Scalable synthesis of the L/N ring of maitotoxin",

abstract = "A scalable method for synthesizing the L/N ring of maitotoxin corresponding to an unnatural L-glucose derivative was developed via the MacMillan method and C-glycosylation under flow conditions. The longest linear sequence from Z-2-buten-1,4-diol was 7 steps with 10 total steps.",

keywords = "L/N ring, Maitotoxin, Microflow reactor, Polyether natural products, ʟ-Glucose derivative",

author = "Masashi Nakamura and Mizuki Jintoku and Hayato Kishigami and Yuki Kitayama and Taishin Taniguchi and Kohei Torikai and Yoko Yasuno and Masayuki Satake and Tohru Oishi",

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year = "2024",

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doi = "10.1016/j.tetlet.2024.155221",

language = "English",

volume = "147",

journal = "Tetrahedron Letters",

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T1 - Scalable synthesis of the L/N ring of maitotoxin

AU - Nakamura, Masashi

AU - Jintoku, Mizuki

AU - Kishigami, Hayato

AU - Kitayama, Yuki

AU - Taniguchi, Taishin

AU - Torikai, Kohei

AU - Yasuno, Yoko

AU - Satake, Masayuki

AU - Oishi, Tohru

PY - 2024/9/1

Y1 - 2024/9/1

N2 - A scalable method for synthesizing the L/N ring of maitotoxin corresponding to an unnatural L-glucose derivative was developed via the MacMillan method and C-glycosylation under flow conditions. The longest linear sequence from Z-2-buten-1,4-diol was 7 steps with 10 total steps.

AB - A scalable method for synthesizing the L/N ring of maitotoxin corresponding to an unnatural L-glucose derivative was developed via the MacMillan method and C-glycosylation under flow conditions. The longest linear sequence from Z-2-buten-1,4-diol was 7 steps with 10 total steps.

KW - L/N ring

KW - Maitotoxin

KW - Microflow reactor

KW - Polyether natural products

KW - ʟ-Glucose derivative

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UR - http://www.scopus.com/inward/citedby.url?scp=85199944727&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2024.155221

DO - 10.1016/j.tetlet.2024.155221

M3 - Article

AN - SCOPUS:85199944727

SN - 0040-4039

VL - 147

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 155221

ER -

Scalable synthesis of the L/N ring of maitotoxin

Abstract

All Science Journal Classification (ASJC) codes

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