Stereocontrolled synthesis of the 6-7-7-6 ring system of polycyclic ethers via the intramolecular reaction with ω-tributylstannyl ether aldehydes

Isao Kadota, Yoshinori Yamamoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

: The BF3.OEt2 mediated cyclization of ω-tributylstannyl ether aldehyde 1 produces seven-membered cyclic ethers 2 in 95% yield with high diastereoselectivity (2a:2b = 93:7). Perfect stereocontrol between a and α’ proton is accomplished in the cyclization to give the cis products, and the stereochemistry between a and p proton is controlled to trans resulting in the predominant formation of the anti isomer 2a. This allylic tin method is applied to the stereocontrolled synthesis of 6,7,7,6-polycyclic ether skeleton as a model synthesis of brevetoxin B.

Original languageEnglish
Pages (from-to)269-289
Number of pages21
JournalMain Group Metal Chemistry
Volume17
Issue number1-4
DOIs
Publication statusPublished - 1994
Externally publishedYes

Fingerprint

Ethers
Cyclization
Aldehydes
aldehydes
Ether
Protons
ethers
Cyclic Ethers
Stereochemistry
Tin
rings
synthesis
Isomers
protons
stereochemistry
musculoskeletal system
tin
isomers
products
brevetoxin B

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Chemistry
  • Metals and Alloys
  • Condensed Matter Physics

Cite this

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abstract = ": The BF3.OEt2 mediated cyclization of ω-tributylstannyl ether aldehyde 1 produces seven-membered cyclic ethers 2 in 95{\%} yield with high diastereoselectivity (2a:2b = 93:7). Perfect stereocontrol between a and α’ proton is accomplished in the cyclization to give the cis products, and the stereochemistry between a and p proton is controlled to trans resulting in the predominant formation of the anti isomer 2a. This allylic tin method is applied to the stereocontrolled synthesis of 6,7,7,6-polycyclic ether skeleton as a model synthesis of brevetoxin B.",
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T1 - Stereocontrolled synthesis of the 6-7-7-6 ring system of polycyclic ethers via the intramolecular reaction with ω-tributylstannyl ether aldehydes

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AU - Yamamoto, Yoshinori

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N2 - : The BF3.OEt2 mediated cyclization of ω-tributylstannyl ether aldehyde 1 produces seven-membered cyclic ethers 2 in 95% yield with high diastereoselectivity (2a:2b = 93:7). Perfect stereocontrol between a and α’ proton is accomplished in the cyclization to give the cis products, and the stereochemistry between a and p proton is controlled to trans resulting in the predominant formation of the anti isomer 2a. This allylic tin method is applied to the stereocontrolled synthesis of 6,7,7,6-polycyclic ether skeleton as a model synthesis of brevetoxin B.

AB - : The BF3.OEt2 mediated cyclization of ω-tributylstannyl ether aldehyde 1 produces seven-membered cyclic ethers 2 in 95% yield with high diastereoselectivity (2a:2b = 93:7). Perfect stereocontrol between a and α’ proton is accomplished in the cyclization to give the cis products, and the stereochemistry between a and p proton is controlled to trans resulting in the predominant formation of the anti isomer 2a. This allylic tin method is applied to the stereocontrolled synthesis of 6,7,7,6-polycyclic ether skeleton as a model synthesis of brevetoxin B.

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