Total synthesis of (-)-brevenal

A streamlined strategy for practical synthesis of polycyclic ethers

Makoto Ebine, Haruhiko Fuwa, Makoto Sasaki

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

We describe a streamlined strategy for the practical synthesis of trans-fused polycyclic ethers and its application to a concise total synthesis of (-)-brevenal, a new pentacyclic polyether natural product with intriguing biological activities. The B-, D-, and E-rings were constructed by TEMPO/PhI(OAc)2-mediated oxidative lactonization of the corresponding 1,6-diols, with minimal need for manipulation of oxygen functionalities. The B- and E-ring lactones were appropriately functionalized by Suzuki-Miyaura coupling of lactone-derived enol phosphates and subsequent stereoselective hydroboration. The A-ring was formed by our mixed thioacetalization methodology. The AB- and DE-ring fragments were assembled through Suzuki-Miyaura coupling, and the C-ring was forged in the same manner as that for the A-ring. More than two grams of the pentacyclic polyether core of (-)-brevenal have been synthesized by the synthetic route developed in this study.

Original languageEnglish
Pages (from-to)13754-13761
Number of pages8
JournalChemistry - A European Journal
Volume17
Issue number49
DOIs
Publication statusPublished - Dec 2 2011

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Ethers
Polyethers
Lactones
Bioactivity
Biological Products
Phosphates
Oxygen
TEMPO

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Total synthesis of (-)-brevenal : A streamlined strategy for practical synthesis of polycyclic ethers. / Ebine, Makoto; Fuwa, Haruhiko; Sasaki, Makoto.

In: Chemistry - A European Journal, Vol. 17, No. 49, 02.12.2011, p. 13754-13761.

Research output: Contribution to journalArticle

Ebine, Makoto ; Fuwa, Haruhiko ; Sasaki, Makoto. / Total synthesis of (-)-brevenal : A streamlined strategy for practical synthesis of polycyclic ethers. In: Chemistry - A European Journal. 2011 ; Vol. 17, No. 49. pp. 13754-13761.
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