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

被引：60

作者：

Kadota, I

Ohno, A

Matsuda, K

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Res Ctr Sustainable Mat Engn, Sendai, Miyagi 9808578, Japan

[2] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 14期

关键词：

D O I：

10.1021/ja025523g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Lewis acid mediated reaction of a-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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页码：3562 / 3566

页数：5

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