Total synthesis of hemibrevetoxin B via the allylic tin methodology

Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The total synthesis of Hemibrevetoxin B is described. A new cyclization approach, based on the Lewis acid mediated intramolecular cyclization of the γ-oxo-substituted allylic tin having an aldehyde group, produced the 6-6-7-7 polycyclic ether skeleton of the natural product with high stereoselectivity. The 1H and 13C-NMR spectra of synthetic hemibrevetoxin B was identical with those of natural product.

Original languageEnglish
Pages (from-to)361-366
Number of pages6
JournalMain Group Metal Chemistry
Volume19
Issue number6
Publication statusPublished - 1996
Externally publishedYes

Fingerprint

Tin
Cyclization
Biological Products
tin
methodology
Stereoselectivity
Lewis Acids
synthesis
products
Aldehydes
aldehydes
musculoskeletal system
Ether
Ethers
ethers
Nuclear magnetic resonance
nuclear magnetic resonance
acids
Acids
hemibrevetoxin B

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Total synthesis of hemibrevetoxin B via the allylic tin methodology. / Kadota, Isao; Yamamoto, Yoshinori.

In: Main Group Metal Chemistry, Vol. 19, No. 6, 1996, p. 361-366.

Research output: Contribution to journalArticle

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