A NEW APPROACH TO THE CONSTRUCTION OF BETA-ALKOXY-SUBSTITUTED CYCLIC ETHERS VIA THE INTRAMOLECULAR CYCLIZATION OF OMEGA-TRIALKYLPLUMBYL AND OMEGA-TRIALKYLSTANNYL ETHER ACETALS

被引：52

作者：

YAMADA, J ^{[1
]}

ASANO, T ^{[1
]}

KADOTA, I ^{[1
]}

YAMAMOTO, Y ^{[1
]}

机构：

[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 25期

关键词：

D O I：

10.1021/jo00312a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: The w-trialkylplumbyl ether acetal (la) gave the β-alkoxy cyclic ether (2a) upon treatment with 2 equiv of TiCl4in CH2C12. The reaction of the ω-trialkylstannyl ether acetals 3, 4, and 5 in the presence of 2 equiv of TiCl3 (OiPr) in CH2C12 produced the corresponding 0-alkoxy- a-vinyl cyclic ethers 6, 7, and 8, respectively. This new procedure permitted the chiral synthesis of a fundamental structural unit (20) of cyclic ether natural products. © 1990, American Chemical Society. All rights reserved.

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页码：6066 / 6068

页数：3

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