Convergent synthesis of the FGHI ring system of yessotoxin: Stereoselective construction of the G ring

Koji Watanabe, Miho Suzuki, Michio Murata, Tohru Oishi

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

A convergent synthetic route to the FGHI ring system of yessotoxin, a marine ladder polyether, has been developed. The synthesis features convergent coupling of the diol and the aldehyde to form α-cyano ethers via acetal formation followed by ring closing metathesis and reductive etherification to construct the oxocane ring G and tetrahydropyran ring H, respectively. The β-methyl group on the G ring was stereoselectively introduced by alkylation of the corresponding ketone.

Original languageEnglish
Pages (from-to)3991-3995
Number of pages5
JournalTetrahedron Letters
Volume46
Issue number23
DOIs
Publication statusPublished - Jun 6 2005
Externally publishedYes

Fingerprint

Acetals
Ethers
Polyethers
Alkylation
Ladders
Ketones
Aldehydes
yessotoxin

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Convergent synthesis of the FGHI ring system of yessotoxin : Stereoselective construction of the G ring. / Watanabe, Koji; Suzuki, Miho; Murata, Michio; Oishi, Tohru.

In: Tetrahedron Letters, Vol. 46, No. 23, 06.06.2005, p. 3991-3995.

Research output: Contribution to journalArticle

Watanabe, Koji ; Suzuki, Miho ; Murata, Michio ; Oishi, Tohru. / Convergent synthesis of the FGHI ring system of yessotoxin : Stereoselective construction of the G ring. In: Tetrahedron Letters. 2005 ; Vol. 46, No. 23. pp. 3991-3995.
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