Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities

Isao Kadota, Hiroyoshi Takamura, Kumi Sato, Akio Ohno, Kumiko Matsuda, Masayuki Satake, Yoshinori Yamamoto

Research output: Contribution to journalArticle

100 Citations (Scopus)

Abstract

The convergent total syntheses of gambierol (1) and 16-epi-gambierol (2) have been achieved. The ABC and FGH ring segments 4 and 5 were prepared from known compounds 6 and 13, respectively, by linear manners. The fragments prepared were connected by our own synthetic strategy including the intramolecular allylation of α-acetoxy ether followed by ring-closing metathesis to furnish the octacyclic ether 3. The diiodoalkene 45, prepared from 3, was converted to the Z-iodoalkene 50 via a novel and stereoselective hydrogenolysis followed by deprotection. Construction of the triene side chain was performed by the modified Stille coupling of 50 with the Z-vinylic stannane 41 to afford 1. The similar transformations were carried out on the epimeric octacycle 34 to give 2, which showed no toxicity against mice at the concentration of 14 mg/kg.

Original languageEnglish
Pages (from-to)11893-11899
Number of pages7
JournalJournal of the American Chemical Society
Volume125
Issue number39
DOIs
Publication statusPublished - Oct 1 2003
Externally publishedYes

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Bioactivity
Ether
Ethers
Allylation
Hydrogenolysis
Toxicity
gambierol
stannane

ASJC Scopus subject areas

  • Chemistry(all)

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Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities. / Kadota, Isao; Takamura, Hiroyoshi; Sato, Kumi; Ohno, Akio; Matsuda, Kumiko; Satake, Masayuki; Yamamoto, Yoshinori.

In: Journal of the American Chemical Society, Vol. 125, No. 39, 01.10.2003, p. 11893-11899.

Research output: Contribution to journalArticle

Kadota, Isao ; Takamura, Hiroyoshi ; Sato, Kumi ; Ohno, Akio ; Matsuda, Kumiko ; Satake, Masayuki ; Yamamoto, Yoshinori. / Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 39. pp. 11893-11899.
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