A formal total synthesis of (+)-pinnatoxin A

Satoshi Sakamoto; Hayato Sakazaki; Koji Hagiwara; Kei Kamada; Kento Ishii; Takeshi Noda; Masayuki Inoue; Masahiro Hirama

doi:10.1002/anie.200461802

A formal total synthesis of (+)-pinnatoxin A

Satoshi Sakamoto, Hayato Sakazaki, Koji Hagiwara, Kei Kamada, Kento Ishii, Takeshi Noda, Masayuki Inoue, Masahiro Hirama

New Industry Creation Hatchery Center (NICHe)

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

57 Citations (Scopus)

Abstract

Powerful dithiane coupling (A) of two fragments and subsequent macrocyclization by ring-closing metathesis (B) produced the entire 27-membered carbocycle of (+)-pinnatoxin A (1), a major toxic principle responsible for outbreaks of shellfish poisonings in China and Japan. (Chemical equation presented).

Original language	English
Pages (from-to)	6505-6510
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	47
DOIs	https://doi.org/10.1002/anie.200461802
Publication status	Published - 2004 Dec 3

Keywords

Heterocycles
Macrocycles
Natural products
Spiro compounds
Total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200461802

Cite this

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abstract = "Powerful dithiane coupling (A) of two fragments and subsequent macrocyclization by ring-closing metathesis (B) produced the entire 27-membered carbocycle of (+)-pinnatoxin A (1), a major toxic principle responsible for outbreaks of shellfish poisonings in China and Japan. (Chemical equation presented).",

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author = "Satoshi Sakamoto and Hayato Sakazaki and Koji Hagiwara and Kei Kamada and Kento Ishii and Takeshi Noda and Masayuki Inoue and Masahiro Hirama",

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T1 - A formal total synthesis of (+)-pinnatoxin A

AU - Sakamoto, Satoshi

AU - Sakazaki, Hayato

AU - Hagiwara, Koji

AU - Kamada, Kei

AU - Ishii, Kento

AU - Noda, Takeshi

AU - Inoue, Masayuki

AU - Hirama, Masahiro

PY - 2004/12/3

Y1 - 2004/12/3

N2 - Powerful dithiane coupling (A) of two fragments and subsequent macrocyclization by ring-closing metathesis (B) produced the entire 27-membered carbocycle of (+)-pinnatoxin A (1), a major toxic principle responsible for outbreaks of shellfish poisonings in China and Japan. (Chemical equation presented).

AB - Powerful dithiane coupling (A) of two fragments and subsequent macrocyclization by ring-closing metathesis (B) produced the entire 27-membered carbocycle of (+)-pinnatoxin A (1), a major toxic principle responsible for outbreaks of shellfish poisonings in China and Japan. (Chemical equation presented).

KW - Heterocycles

KW - Macrocycles

KW - Natural products

KW - Spiro compounds

KW - Total synthesis

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U2 - 10.1002/anie.200461802

DO - 10.1002/anie.200461802

M3 - Article

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EP - 6510

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 47

ER -

A formal total synthesis of (+)-pinnatoxin A

Abstract

Keywords

ASJC Scopus subject areas

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