Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin

Daisuke Matsumura; Toshimasa Takarabe; Takumi Toda; Takashi Hayamizu; Kiyoto Sawamura; Ken Ichi Takao; Kin Ichi Tadano

doi:10.1016/j.tet.2011.04.006

Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin

Daisuke Matsumura, Toshimasa Takarabe, Takumi Toda, Takashi Hayamizu, Kiyoto Sawamura, Ken Ichi Takao, Kin Ichi Tadano

Department of Applied Chemistry

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

6 Citations (Scopus)

Abstract

The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels-Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton. A stereocongener of (+)-spiculoic acid A, i.e., the (2R,5S,6R)-isomer, was also synthesized. The details of these total syntheses are described.

Original language	English
Pages (from-to)	6730-6745
Number of pages	16
Journal	Tetrahedron
Volume	67
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2011.04.006
Publication status	Published - 2011 Sept 2

Keywords

(+)-Spiculoic acid A
(+)-Zyggomphic acid
Cytotoxicity
Intramolecular reaction Diels-Alder reaction
Marine natural product

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.tet.2011.04.006

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title = "Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin",

abstract = "The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels-Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton. A stereocongener of (+)-spiculoic acid A, i.e., the (2R,5S,6R)-isomer, was also synthesized. The details of these total syntheses are described.",

keywords = "(+)-Spiculoic acid A, (+)-Zyggomphic acid, Cytotoxicity, Intramolecular reaction Diels-Alder reaction, Marine natural product",

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

note = "Funding Information: This article is dedicated to Professor Satoshi Ōmura with admiration and respect on the occasion of his receipt of the 2010 Tetrahedron Prize for Creativity in Organic Chemistry. 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.",

year = "2011",

month = sep,

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doi = "10.1016/j.tet.2011.04.006",

language = "English",

volume = "67",

pages = "6730--6745",

journal = "Tetrahedron",

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T1 - Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin

AU - Matsumura, Daisuke

AU - Takarabe, Toshimasa

AU - Toda, Takumi

AU - Hayamizu, Takashi

AU - Sawamura, Kiyoto

AU - Takao, Ken Ichi

AU - Tadano, Kin Ichi

N1 - Funding Information: This article is dedicated to Professor Satoshi Ōmura with admiration and respect on the occasion of his receipt of the 2010 Tetrahedron Prize for Creativity in Organic Chemistry. 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 - 2011/9/2

Y1 - 2011/9/2

N2 - The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels-Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton. A stereocongener of (+)-spiculoic acid A, i.e., the (2R,5S,6R)-isomer, was also synthesized. The details of these total syntheses are described.

AB - The total syntheses of both natural (+)-spiculoic acid A and (+)-zyggomphic acid, new cytotoxic marine natural products of polyketide origin, have been accomplished for the first time. These syntheses were achieved by the highly stereoselective and high-yielding intramolecular Diels-Alder reaction of a functionalized (E,E,E)-2,7,9-dodecanal derivative to construct the core tetrahydroindan-2-one skeleton. A stereocongener of (+)-spiculoic acid A, i.e., the (2R,5S,6R)-isomer, was also synthesized. The details of these total syntheses are described.

KW - (+)-Spiculoic acid A

KW - (+)-Zyggomphic acid

KW - Cytotoxicity

KW - Intramolecular reaction Diels-Alder reaction

KW - Marine natural product

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M3 - Article

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JO - Tetrahedron

JF - Tetrahedron

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ER -

Total syntheses of (+)-spiculoic acid A and (+)-zyggomphic acid, new marine natural products of polyketide origin

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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