Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides

Yutaka Matsuda, Takayuki Koyama, Masaya Kato, Tomonori Kawaguchi, Yoko Saikawa, Masaya Nakata

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

5-exo-Dig versus 6-endo-dig oxycyclizations of alkynols having an internal triple bond catalyzed by PdCl2, followed by methoxycarbonylation of the resulting vinylpalladium intermediates, are described. With an aim toward the total synthesis of polymaxenolides, a hybrid marine natural product containing a dihydropyran substructure, a model alkynol having the africane-type sesquiterpenoid skeleton was treated with PdCl2 and 1,4-benzoquinone in MeOH under an atmosphere of CO (balloon) to afford the desired 6-endo-dig oxycyclization-methoxycarbonylation product.

Original languageEnglish
Pages (from-to)2134-2148
Number of pages15
JournalTetrahedron
Volume71
Issue number14
DOIs
Publication statusPublished - 2015 Apr 8

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Palladium
Balloons
Carbon Monoxide
Biological Products
Atmosphere
Skeleton
palladium chloride
benzoquinone

Keywords

  • 5-exo-Dig
  • 6-endo-Dig
  • Oxycyclization-methoxycarbonylation
  • Polymaxenolide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides. / Matsuda, Yutaka; Koyama, Takayuki; Kato, Masaya; Kawaguchi, Tomonori; Saikawa, Yoko; Nakata, Masaya.

In: Tetrahedron, Vol. 71, No. 14, 08.04.2015, p. 2134-2148.

Research output: Contribution to journalArticle

Matsuda, Yutaka ; Koyama, Takayuki ; Kato, Masaya ; Kawaguchi, Tomonori ; Saikawa, Yoko ; Nakata, Masaya. / Palladium-catalyzed 6-endo-dig oxycyclization-methoxycarbonylation toward the total synthesis of polymaxenolides. In: Tetrahedron. 2015 ; Vol. 71, No. 14. pp. 2134-2148.
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