Convergent synthesis of the BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ethers

Kazushi Sato; Makoto Sasaki

doi:10.1016/j.tet.2007.02.039

Convergent synthesis of the BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ethers

Kazushi Sato, Makoto Sasaki

LIF - Molecular and Chemical Life Science

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

21 Citations (Scopus)

Abstract

A convergent synthesis of the nonacyclic BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ether marine natural products, has been achieved. The present synthesis involved as key features: (i) convergent union of the BCD- and GHIJ-ring fragments through esterification, (ii) construction of the E-ring as a lactone form via reductive acetylation, (iii) stereoselective allylation to establish the C26 stereocenter, and (iv) ring-closing metathesis reaction to form the nine-membered F-ring.

Original language	English
Pages (from-to)	5977-6003
Number of pages	27
Journal	Tetrahedron
Volume	63
Issue number	26
DOIs	https://doi.org/10.1016/j.tet.2007.02.039
Publication status	Published - 2007 Jun 25

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Convergent synthesis of the BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ethers",

abstract = "A convergent synthesis of the nonacyclic BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ether marine natural products, has been achieved. The present synthesis involved as key features: (i) convergent union of the BCD- and GHIJ-ring fragments through esterification, (ii) construction of the E-ring as a lactone form via reductive acetylation, (iii) stereoselective allylation to establish the C26 stereocenter, and (iv) ring-closing metathesis reaction to form the nine-membered F-ring.",

author = "Kazushi Sato and Makoto Sasaki",

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AU - Sato, Kazushi

AU - Sasaki, Makoto

PY - 2007/6/25

Y1 - 2007/6/25

N2 - A convergent synthesis of the nonacyclic BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ether marine natural products, has been achieved. The present synthesis involved as key features: (i) convergent union of the BCD- and GHIJ-ring fragments through esterification, (ii) construction of the E-ring as a lactone form via reductive acetylation, (iii) stereoselective allylation to establish the C26 stereocenter, and (iv) ring-closing metathesis reaction to form the nine-membered F-ring.

AB - A convergent synthesis of the nonacyclic BCDEFGHIJ-ring polyether core of gambieric acids, potent antifungal polycyclic ether marine natural products, has been achieved. The present synthesis involved as key features: (i) convergent union of the BCD- and GHIJ-ring fragments through esterification, (ii) construction of the E-ring as a lactone form via reductive acetylation, (iii) stereoselective allylation to establish the C26 stereocenter, and (iv) ring-closing metathesis reaction to form the nine-membered F-ring.

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