Total synthesis of (+)-spiculoic acid A

Daisuke Matsumura; Takumi Toda; Takashi Hayamizu; Kiyoto Sawamura; Ken ichi Takao; Kin ichi Tadano

doi:10.1016/j.tetlet.2009.02.101

Total synthesis of (+)-spiculoic acid A

Daisuke Matsumura, Takumi Toda, Takashi Hayamizu, Kiyoto Sawamura, Ken ichi Takao, Kin ichi Tadano

Department of Applied Chemistry

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

15 Citations (Scopus)

Abstract

The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereoselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton.

Original language	English
Pages (from-to)	3356-3358
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2009.02.101
Publication status	Published - 2009 Jul 1

Keywords

(+)-Spiculoic acid A
Cytotoxicity
Intramolecular Diels-Alder reaction
Marine natural product
Suzuki-Miyaura coupling
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2009.02.101

Cite this

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title = "Total synthesis of (+)-spiculoic acid A",

abstract = "The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereoselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton.",

keywords = "(+)-Spiculoic acid A, Cytotoxicity, Intramolecular Diels-Alder reaction, Marine natural product, Suzuki-Miyaura coupling, Total synthesis",

author = "Daisuke Matsumura and Takumi Toda and Takashi Hayamizu and Kiyoto Sawamura and Takao, {Ken ichi} and Tadano, {Kin ichi}",

note = "Funding Information: This work was supported by Grants-in-Aid for Scientific Research on Priority Areas (A) {\textquoteleft}Creation of Biologically Functional Molecules (18032069){\textquoteright} from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. ",

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doi = "10.1016/j.tetlet.2009.02.101",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - Total synthesis of (+)-spiculoic acid A

AU - Matsumura, Daisuke

AU - Toda, Takumi

AU - Hayamizu, Takashi

AU - Sawamura, Kiyoto

AU - Takao, Ken ichi

AU - Tadano, Kin ichi

N1 - Funding Information: This work was supported by Grants-in-Aid for Scientific Research on Priority Areas (A) ‘Creation of Biologically Functional Molecules (18032069)’ from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

PY - 2009/7/1

Y1 - 2009/7/1

N2 - The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereoselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton.

AB - The total synthesis of natural (+)-spiculoic acid A, a new cytotoxic marine natural product of polyketide origin, has been accomplished for the first time. The key step of the total synthesis was a stereoselective and high-yielding intramolecular Diels-Alder reaction of a highly functionalized (E,E,E)-2,7,9-dodecanal derivative for the construction of the core tetrahydroindan-2-one skeleton.

KW - (+)-Spiculoic acid A

KW - Cytotoxicity

KW - Intramolecular Diels-Alder reaction

KW - Marine natural product

KW - Suzuki-Miyaura coupling

KW - Total synthesis

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Total synthesis of (+)-spiculoic acid A

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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