Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: Convergent synthesis of a fully elaborated GHIJ-ring fragment

Koichi Tsubone; Keisuke Hashizume; Haruhiko Fuwa; Makoto Sasaki

doi:10.1016/j.tet.2011.05.082

Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: Convergent synthesis of a fully elaborated GHIJ-ring fragment

Koichi Tsubone, Keisuke Hashizume, Haruhiko Fuwa, Makoto Sasaki

LIF - Molecular and Chemical Life Science

Tohoku University

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

16 Citations (Scopus)

Abstract

A stereocontrolled synthesis of a fully elaborated GHIJ-ring fragment of gambieric acids, which are potent antifungal polycyclic ether natural products, has been accomplished. The synthesis features convergent assembly of the tetracyclic polyether skeleton through aldol coupling/cyclodehydration/reductive etherification processes and stereoselective construction of the J-ring side chain by a CeCl₃-promoted Julia-Kocienski olefination.

Original language	English
Pages (from-to)	6600-6615
Number of pages	16
Journal	Tetrahedron
Volume	67
Issue number	35
DOIs	https://doi.org/10.1016/j.tet.2011.05.082
Publication status	Published - 2011 Sept 2

Keywords

Convergent synthesis
Gambieric acids
Julia-Kocienski olefination
Polycyclic ethers

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10.1016/j.tet.2011.05.082

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title = "Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: Convergent synthesis of a fully elaborated GHIJ-ring fragment",

abstract = "A stereocontrolled synthesis of a fully elaborated GHIJ-ring fragment of gambieric acids, which are potent antifungal polycyclic ether natural products, has been accomplished. The synthesis features convergent assembly of the tetracyclic polyether skeleton through aldol coupling/cyclodehydration/reductive etherification processes and stereoselective construction of the J-ring side chain by a CeCl3-promoted Julia-Kocienski olefination.",

keywords = "Convergent synthesis, Gambieric acids, Julia-Kocienski olefination, Polycyclic ethers",

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

note = "Funding Information: We thank Dr. Y. Kasai (Tohoku University) for measurement of NMR spectra. 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, potent antifungal polycyclic ethers

T2 - Convergent synthesis of a fully elaborated GHIJ-ring fragment

AU - Tsubone, Koichi

AU - Hashizume, Keisuke

AU - Fuwa, Haruhiko

AU - Sasaki, Makoto

N1 - Funding Information: We thank Dr. Y. Kasai (Tohoku University) for measurement of NMR spectra. 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 - 2011/9/2

Y1 - 2011/9/2

N2 - A stereocontrolled synthesis of a fully elaborated GHIJ-ring fragment of gambieric acids, which are potent antifungal polycyclic ether natural products, has been accomplished. The synthesis features convergent assembly of the tetracyclic polyether skeleton through aldol coupling/cyclodehydration/reductive etherification processes and stereoselective construction of the J-ring side chain by a CeCl3-promoted Julia-Kocienski olefination.

AB - A stereocontrolled synthesis of a fully elaborated GHIJ-ring fragment of gambieric acids, which are potent antifungal polycyclic ether natural products, has been accomplished. The synthesis features convergent assembly of the tetracyclic polyether skeleton through aldol coupling/cyclodehydration/reductive etherification processes and stereoselective construction of the J-ring side chain by a CeCl3-promoted Julia-Kocienski olefination.

KW - Convergent synthesis

KW - Gambieric acids

KW - Julia-Kocienski olefination

KW - Polycyclic ethers

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Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: Convergent synthesis of a fully elaborated GHIJ-ring fragment

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Keywords

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