Studies toward the total synthesis of gambieric acids: Convergent synthesis of the GHIJ-ring fragment having a side chain

Koichi Tsubone; Keisuke Hashizume; Haruhiko Fuwa; Makoto Sasaki

doi:10.1016/j.tetlet.2010.11.127

Studies toward the total synthesis of gambieric acids: Convergent synthesis of the GHIJ-ring fragment having a side chain

Koichi Tsubone, Keisuke Hashizume, Haruhiko Fuwa, Makoto Sasaki

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

12 Citations (Scopus)

Abstract

A stereocontrolled synthesis of the GHIJ-ring fragment having a side chain of gambieric acids, which are potent antifungal polycyclic ether natural products, has been achieved. The synthesis features convergent assembly of the tetracyclic polyether skeleton by using aldol coupling and stereoselective construction of the J-ring side chain by a cerium chloride-promoted Julia-Kocienski reaction.

Original language	English
Pages (from-to)	548-551
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	4
DOIs	https://doi.org/10.1016/j.tetlet.2010.11.127
Publication status	Published - 2011 Jan 26

Keywords

Aldol coupling
Gambieric acids
Julia-Kocienski reaction
Polycyclic ethers

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Studies toward the total synthesis of gambieric acids: Convergent synthesis of the GHIJ-ring fragment having a side chain",

abstract = "A stereocontrolled synthesis of the GHIJ-ring fragment having a side chain of gambieric acids, which are potent antifungal polycyclic ether natural products, has been achieved. The synthesis features convergent assembly of the tetracyclic polyether skeleton by using aldol coupling and stereoselective construction of the J-ring side chain by a cerium chloride-promoted Julia-Kocienski reaction.",

keywords = "Aldol coupling, Gambieric acids, Julia-Kocienski reaction, Polycyclic ethers",

author = "Koichi Tsubone and Keisuke Hashizume and Haruhiko Fuwa and Makoto Sasaki",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (A) (No. 21241050 ) from the Japan Society for the Promotion of Science (JSPS). A research fellowship for K.T. from JSPS is thankfully acknowledged.",

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T1 - Studies toward the total synthesis of gambieric acids

T2 - Convergent synthesis of the GHIJ-ring fragment having a side chain

AU - Tsubone, Koichi

AU - Hashizume, Keisuke

AU - Fuwa, Haruhiko

AU - Sasaki, Makoto

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (A) (No. 21241050 ) from the Japan Society for the Promotion of Science (JSPS). A research fellowship for K.T. from JSPS is thankfully acknowledged.

PY - 2011/1/26

Y1 - 2011/1/26

N2 - A stereocontrolled synthesis of the GHIJ-ring fragment having a side chain of gambieric acids, which are potent antifungal polycyclic ether natural products, has been achieved. The synthesis features convergent assembly of the tetracyclic polyether skeleton by using aldol coupling and stereoselective construction of the J-ring side chain by a cerium chloride-promoted Julia-Kocienski reaction.

AB - A stereocontrolled synthesis of the GHIJ-ring fragment having a side chain of gambieric acids, which are potent antifungal polycyclic ether natural products, has been achieved. The synthesis features convergent assembly of the tetracyclic polyether skeleton by using aldol coupling and stereoselective construction of the J-ring side chain by a cerium chloride-promoted Julia-Kocienski reaction.

KW - Aldol coupling

KW - Gambieric acids

KW - Julia-Kocienski reaction

KW - Polycyclic ethers

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Studies toward the total synthesis of gambieric acids: Convergent synthesis of the GHIJ-ring fragment having a side chain

Abstract

Keywords

ASJC Scopus subject areas

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