Convergent synthesis of polycyclic ethers via the intramolecular allylation of α-acetoxy ethers and subsequent ring-closing metathesis

Isao Kadota, Akio Ohno, Kumiko Matsuda, Yoshinori Yamamoto

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

The Lewis acid mediated reaction of α-acetoxy ethers 15-22 gave the corresponding cyclized products 23, 25, 27, 29, 31, 32, 34, and 36 in good yields with high stereoselectivities. Those cyclized products were subjected to ring-closing metathesis to afford the polycyclic ethers 38-42, 44, and 45 in good yields. The usefulness of the present methodology was demonstrated by the convergent synthesis of the CDEF ring system of brevetoxin B (1) and the CDEFG ring system of gambierol (2).

Original languageEnglish
Pages (from-to)3562-3566
Number of pages5
JournalJournal of the American Chemical Society
Volume124
Issue number14
DOIs
Publication statusPublished - Apr 10 2002
Externally publishedYes

Fingerprint

Allylation
Ethers
Stereoselectivity
Lewis Acids
Acids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Convergent synthesis of polycyclic ethers via the intramolecular allylation of α-acetoxy ethers and subsequent ring-closing metathesis. / Kadota, Isao; Ohno, Akio; Matsuda, Kumiko; Yamamoto, Yoshinori.

In: Journal of the American Chemical Society, Vol. 124, No. 14, 10.04.2002, p. 3562-3566.

Research output: Contribution to journalArticle

@article{e68026178fb34299acd6e700a2ff7333,
title = "Convergent synthesis of polycyclic ethers via the intramolecular allylation of α-acetoxy ethers and subsequent ring-closing metathesis",
abstract = "The Lewis acid mediated reaction of α-acetoxy ethers 15-22 gave the corresponding cyclized products 23, 25, 27, 29, 31, 32, 34, and 36 in good yields with high stereoselectivities. Those cyclized products were subjected to ring-closing metathesis to afford the polycyclic ethers 38-42, 44, and 45 in good yields. The usefulness of the present methodology was demonstrated by the convergent synthesis of the CDEF ring system of brevetoxin B (1) and the CDEFG ring system of gambierol (2).",
author = "Isao Kadota and Akio Ohno and Kumiko Matsuda and Yoshinori Yamamoto",
year = "2002",
month = "4",
day = "10",
doi = "10.1021/ja025523g",
language = "English",
volume = "124",
pages = "3562--3566",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "14",

}

TY - JOUR

T1 - Convergent synthesis of polycyclic ethers via the intramolecular allylation of α-acetoxy ethers and subsequent ring-closing metathesis

AU - Kadota, Isao

AU - Ohno, Akio

AU - Matsuda, Kumiko

AU - Yamamoto, Yoshinori

PY - 2002/4/10

Y1 - 2002/4/10

N2 - The Lewis acid mediated reaction of α-acetoxy ethers 15-22 gave the corresponding cyclized products 23, 25, 27, 29, 31, 32, 34, and 36 in good yields with high stereoselectivities. Those cyclized products were subjected to ring-closing metathesis to afford the polycyclic ethers 38-42, 44, and 45 in good yields. The usefulness of the present methodology was demonstrated by the convergent synthesis of the CDEF ring system of brevetoxin B (1) and the CDEFG ring system of gambierol (2).

AB - The Lewis acid mediated reaction of α-acetoxy ethers 15-22 gave the corresponding cyclized products 23, 25, 27, 29, 31, 32, 34, and 36 in good yields with high stereoselectivities. Those cyclized products were subjected to ring-closing metathesis to afford the polycyclic ethers 38-42, 44, and 45 in good yields. The usefulness of the present methodology was demonstrated by the convergent synthesis of the CDEF ring system of brevetoxin B (1) and the CDEFG ring system of gambierol (2).

UR - http://www.scopus.com/inward/record.url?scp=0037051647&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037051647&partnerID=8YFLogxK

U2 - 10.1021/ja025523g

DO - 10.1021/ja025523g

M3 - Article

C2 - 11929244

AN - SCOPUS:0037051647

VL - 124

SP - 3562

EP - 3566

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 14

ER -