Synthetic studies of yessotoxin: Stereoselective annulation of the CD and JK ring fragments by using Pd(II)-catalyzed cyclization

Hajime Yokoyama; Genki Moriyama; Kazuki Nishida; Yasuhiro Kusumoto; Kiyoshi Tsuge; Masahiro Miyazawa; Yoshiro Hirai

doi:10.3987/COM-17-13858

Synthetic studies of yessotoxin: Stereoselective annulation of the CD and JK ring fragments by using Pd(II)-catalyzed cyclization

Hajime Yokoyama^*, Genki Moriyama, Kazuki Nishida, Yasuhiro Kusumoto, Kiyoshi Tsuge, Masahiro Miyazawa, Yoshiro Hirai

^*Corresponding author for this work

Department of Chemistry

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

4 Scopus citations

Abstract

Yessotoxin is the polycyclic ether implicated in diarrheic shellfish poisoning. This toxin has A-K ring system involving 6-, 7-, 8-membered ether rings. We have been studying high stereoselective Pd(II)-catalyzed cyclization. Herein we describe the CD and JK ring fragments of yessotoxin by our annulation based on Pd(II)-catalyzed cyclization. The efforts to understand these high stereoselectivities are also disclosed. This annulation method could be applicable to other polyethers and related natural products.

Original language	English
Pages (from-to)	470-482
Number of pages	13
Journal	Heterocycles
Volume	96
Issue number	3
DOIs	https://doi.org/10.3987/COM-17-13858
State	Published - 2018

ASJC Scopus subject areas

Organic Chemistry
Drug Discovery

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title = "Synthetic studies of yessotoxin: Stereoselective annulation of the CD and JK ring fragments by using Pd(II)-catalyzed cyclization",

abstract = "Yessotoxin is the polycyclic ether implicated in diarrheic shellfish poisoning. This toxin has A-K ring system involving 6-, 7-, 8-membered ether rings. We have been studying high stereoselective Pd(II)-catalyzed cyclization. Herein we describe the CD and JK ring fragments of yessotoxin by our annulation based on Pd(II)-catalyzed cyclization. The efforts to understand these high stereoselectivities are also disclosed. This annulation method could be applicable to other polyethers and related natural products.",

author = "Hajime Yokoyama and Genki Moriyama and Kazuki Nishida and Yasuhiro Kusumoto and Kiyoshi Tsuge and Masahiro Miyazawa and Yoshiro Hirai",

note = "Publisher Copyright: {\textcopyright} 2018 The Japan Institute of Heterocyclic Chemistry.",

year = "2018",

doi = "10.3987/COM-17-13858",

language = "英語",

volume = "96",

pages = "470--482",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

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TY - JOUR

T1 - Synthetic studies of yessotoxin

T2 - Stereoselective annulation of the CD and JK ring fragments by using Pd(II)-catalyzed cyclization

AU - Yokoyama, Hajime

AU - Moriyama, Genki

AU - Nishida, Kazuki

AU - Kusumoto, Yasuhiro

AU - Tsuge, Kiyoshi

AU - Miyazawa, Masahiro

AU - Hirai, Yoshiro

PY - 2018

Y1 - 2018

N2 - Yessotoxin is the polycyclic ether implicated in diarrheic shellfish poisoning. This toxin has A-K ring system involving 6-, 7-, 8-membered ether rings. We have been studying high stereoselective Pd(II)-catalyzed cyclization. Herein we describe the CD and JK ring fragments of yessotoxin by our annulation based on Pd(II)-catalyzed cyclization. The efforts to understand these high stereoselectivities are also disclosed. This annulation method could be applicable to other polyethers and related natural products.

AB - Yessotoxin is the polycyclic ether implicated in diarrheic shellfish poisoning. This toxin has A-K ring system involving 6-, 7-, 8-membered ether rings. We have been studying high stereoselective Pd(II)-catalyzed cyclization. Herein we describe the CD and JK ring fragments of yessotoxin by our annulation based on Pd(II)-catalyzed cyclization. The efforts to understand these high stereoselectivities are also disclosed. This annulation method could be applicable to other polyethers and related natural products.

UR - http://www.scopus.com/inward/record.url?scp=85044287631&partnerID=8YFLogxK

U2 - 10.3987/COM-17-13858

DO - 10.3987/COM-17-13858

M3 - 学術論文

AN - SCOPUS:85044287631

SN - 0385-5414

VL - 96

SP - 470

EP - 482

JO - Heterocycles

JF - Heterocycles

IS - 3

ER -

Synthetic studies of yessotoxin: Stereoselective annulation of the CD and JK ring fragments by using Pd(II)-catalyzed cyclization

Abstract

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