Stereocontrolled synthesis of polycyclic ethers and related heterocycles via the intramolecular reaction of allylstannanes

Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The synthetic reaction using functionalized allylstannanes is widely appreciated as one of the most useful methods for the stereocontrolled C-C bond formation. We now report the stereoselective synthesis of functionalized heterocycles via the intramolecular reaction of allylstannane with aldehydes and imines. The stereocontrolled total synthesis of hemibrevetoxin B was achieved by using the intramolecular reaction of γ-alkoxyallylstannane with aldehydes. The extension of this methodology led to a new strategy for the stereoselective synthesis of alkaloids such as (+)-desoxoprosopinine and (+)-preussin.

Original languageEnglish
Pages (from-to)619-630
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume55
Issue number7
Publication statusPublished - Jul 1997
Externally publishedYes

Fingerprint

Ethers
preussin
Aldehydes
Imines
Alkaloids

Keywords

  • (+)-Desoxoprosopinine
  • (+)-Preussin
  • Alkaloid
  • Allylstannane
  • Hemibrevetoxin B
  • Intramolecular reaction
  • Polycyclic ether

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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AU - Kadota, Isao

AU - Yamamoto, Yoshinori

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KW - Polycyclic ether

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