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

doi:10.1021/ja025523g

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 journal › Article › peer-review

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 language	English
Pages (from-to)	3562-3566
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	124
Issue number	14
DOIs	https://doi.org/10.1021/ja025523g
Publication status	Published - Apr 10 2002
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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).",

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AU - Kadota, Isao

AU - Ohno, Akio

AU - Matsuda, Kumiko

AU - Yamamoto, Yoshinori

PY - 2002/4/10

Y1 - 2002/4/10

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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).

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