Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

Shoji Kobayashi; Yusuke Takahashi; Kazuo Komano; Babak H. Alizadeh; Yuuya Kawada; Tohru Oishi; Shin Ichiro Tanaka; Yoshihiro Ogasawara; Shin Ya Sasaki; Masahiro Hirama

doi:10.1016/j.tet.2004.07.010

Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

Shoji Kobayashi, Yusuke Takahashi, Kazuo Komano, Babak H. Alizadeh, Yuuya Kawada, Tohru Oishi, Shin Ichiro Tanaka, Yoshihiro Ogasawara, Shin Ya Sasaki, Masahiro Hirama

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

41 Citations (Scopus)

Abstract

The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. Graphical Abstract.

Original language	English
Pages (from-to)	8375-8396
Number of pages	22
Journal	Tetrahedron
Volume	60
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2004.07.010
Publication status	Published - Sept 13 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C",

abstract = "The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. Graphical Abstract.",

author = "Shoji Kobayashi and Yusuke Takahashi and Kazuo Komano and Alizadeh, {Babak H.} and Yuuya Kawada and Tohru Oishi and Tanaka, {Shin Ichiro} and Yoshihiro Ogasawara and Sasaki, {Shin Ya} and Masahiro Hirama",

note = "Funding Information: This work was supported by the CREST and SORST programs from the Japan Science and Technology Corporation (JST) and by a Grant-in-Aid for Scientific Research (S) from the Japan Society for the Promotion of Science (JSPS). Fellowships to S. K. and S. S. from JSPS are also acknowledged.",

year = "2004",

month = sep,

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doi = "10.1016/j.tet.2004.07.010",

language = "English",

volume = "60",

pages = "8375--8396",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

AU - Kobayashi, Shoji

AU - Takahashi, Yusuke

AU - Komano, Kazuo

AU - Alizadeh, Babak H.

AU - Kawada, Yuuya

AU - Oishi, Tohru

AU - Tanaka, Shin Ichiro

AU - Ogasawara, Yoshihiro

AU - Sasaki, Shin Ya

AU - Hirama, Masahiro

N1 - Funding Information: This work was supported by the CREST and SORST programs from the Japan Science and Technology Corporation (JST) and by a Grant-in-Aid for Scientific Research (S) from the Japan Society for the Promotion of Science (JSPS). Fellowships to S. K. and S. S. from JSPS are also acknowledged.

PY - 2004/9/13

Y1 - 2004/9/13

N2 - The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. Graphical Abstract.

AB - The ABCDE ring moiety of ciguatoxin CTX3C, a major causative agent of ciguatera poisoning, was stereoselectively synthesized. The key transformations are a chiral auxiliary-based asymmetric alkylation and an asymmetric aldol condensation, which controlled the formation of the C11 and C21-stereocenters, respectively. A highly practical and efficient route to the ABCD ring fragment, a common precursor for the divergent synthesis of the left wings of ciguatoxins, was also established. Graphical Abstract.

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DO - 10.1016/j.tet.2004.07.010

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SP - 8375

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JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Stereocontrolled synthesis of the ABCDE ring moiety of ciguatoxin CTX3C

Abstract

All Science Journal Classification (ASJC) codes

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