Synthetic studies on polymaxenolides: Model studies for constructing dihydropyran portion and synthesis of lower portion

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

With a goal of the total synthesis of polymaxenolide, the first hybrid marine natural product, the model studies for constructing the dihydropyran portion based on the originally proposed biosynthesis (C-C bond formation followed by dehydrative cyclization) and the synthesis of the lower portion (the C1-C3, C7-C17 portion) based on an iodide-induced Morita-Baylis-Hillman type reaction (a three-component assembly) followed by Suzuki-Miyaura cross-coupling are described.

Original languageEnglish
Pages (from-to)1154-1168
Number of pages15
JournalTetrahedron
Volume70
Issue number6
DOIs
Publication statusPublished - 2014 Feb 11

Fingerprint

Iodides
Cyclization
Biological Products
Biosynthesis

Keywords

  • Dehydrative cyclization
  • Morita-Baylis-Hillman reaction
  • Polymaxenolide
  • Suzuki-Miyaura cross-coupling

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthetic studies on polymaxenolides : Model studies for constructing dihydropyran portion and synthesis of lower portion. / Matsuda, Yutaka; Kato, Masaya; Kawaguchi, Tomonori; Koyama, Takayuki; Saikawa, Yoko; Nakata, Masaya.

In: Tetrahedron, Vol. 70, No. 6, 11.02.2014, p. 1154-1168.

Research output: Contribution to journalArticle

Matsuda, Yutaka ; Kato, Masaya ; Kawaguchi, Tomonori ; Koyama, Takayuki ; Saikawa, Yoko ; Nakata, Masaya. / Synthetic studies on polymaxenolides : Model studies for constructing dihydropyran portion and synthesis of lower portion. In: Tetrahedron. 2014 ; Vol. 70, No. 6. pp. 1154-1168.
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