Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

Kentaro Takai; Tadaatsu Hanadate; Masaki Abe; Yukie Ono; Teiko Yamada; Shigefumi Kuwahara; Hiromasa Kiyota

doi:10.1016/j.tet.2011.07.012

Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

Kentaro Takai, Tadaatsu Hanadate, Masaki Abe, Yukie Ono, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

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

6 Citations (Scopus)

Abstract

Macrotetrolide α (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners.

Original language	English
Pages (from-to)	7066-7072
Number of pages	7
Journal	Tetrahedron
Volume	67
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2011.07.012
Publication status	Published - Sept 16 2011
Externally published	Yes

Keywords

Antibiotics
Bishomononactic acid
Macrotetrolides
Polynactin
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.07.012

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title = "Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids",

abstract = "Macrotetrolide α (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners.",

keywords = "Antibiotics, Bishomononactic acid, Macrotetrolides, Polynactin, Total synthesis",

author = "Kentaro Takai and Tadaatsu Hanadate and Masaki Abe and Yukie Ono and Teiko Yamada and Shigefumi Kuwahara and Hiromasa Kiyota",

note = "Funding Information: Financial supports by grant-in-aid from Japan Society for the Promotion of Science (No. 17580092 and 19580120 ), The Agricultural Chemical Research Foundation , Intelligent Cosmos Foundation and The Naito Foundation is gratefully acknowledged. ",

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doi = "10.1016/j.tet.2011.07.012",

language = "English",

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T1 - Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

AU - Takai, Kentaro

AU - Hanadate, Tadaatsu

AU - Abe, Masaki

AU - Ono, Yukie

AU - Yamada, Teiko

AU - Kuwahara, Shigefumi

AU - Kiyota, Hiromasa

N1 - Funding Information: Financial supports by grant-in-aid from Japan Society for the Promotion of Science (No. 17580092 and 19580120 ), The Agricultural Chemical Research Foundation , Intelligent Cosmos Foundation and The Naito Foundation is gratefully acknowledged.

PY - 2011/9/16

Y1 - 2011/9/16

N2 - Macrotetrolide α (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners.

AB - Macrotetrolide α (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners.

KW - Antibiotics

KW - Bishomononactic acid

KW - Macrotetrolides

KW - Polynactin

KW - Total synthesis

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DO - 10.1016/j.tet.2011.07.012

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JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

Abstract

Keywords

ASJC Scopus subject areas

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