A facile and practical synthesis of Nicolaou's key intermediates, 2-methyl- and 2,6-dimethyltetrahydropyrans, toward the total synthesis of ladder-shaped polyethers

Takeharu Nakashima, Tomomi Baba, Hisaaki Onoue, Wataru Yamashita, Kohei Torikai

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A facile and robust method to prepare 2-methyl- and 2,6- dimethyltetrahydropyrans, most useful Nicolaou intermediates for the synthesis of ladder-shaped polyethers, is disclosed. The established highly practical recipe, adopting chemo- and stereoselective catalytic oxidations and one-pot reactions with few chromatographic purifications, would significantly facilitate the large-scale supply of pivotal monocyclic building blocks, which is a rate-determining process of gigantic tetrahydropyran-containing natural products synthesis.

Original languageEnglish
Article numberSS-2013-F0387-OP
Pages (from-to)2417-2425
Number of pages9
JournalSynthesis (Germany)
Volume45
Issue number17
DOIs
Publication statusPublished - Jul 24 2013

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Polyethers
Ladders
Catalytic oxidation
Biological Products
Purification

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

A facile and practical synthesis of Nicolaou's key intermediates, 2-methyl- and 2,6-dimethyltetrahydropyrans, toward the total synthesis of ladder-shaped polyethers. / Nakashima, Takeharu; Baba, Tomomi; Onoue, Hisaaki; Yamashita, Wataru; Torikai, Kohei.

In: Synthesis (Germany), Vol. 45, No. 17, SS-2013-F0387-OP, 24.07.2013, p. 2417-2425.

Research output: Contribution to journalArticle

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