A facile synthesis of aryldihydropyrans using a Sonogashira-selenoetherification strategy

被引：22

作者：

Brimble, MA ^{[1
]}

Pavia, GS ^{[1
]}

Stevenson, RJ ^{[1
]}

机构：

[1] Univ Auckland, Dept Chem, Auckland 1, New Zealand

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(02)00065-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A high yielding and convenient synthesis of 2-aryl-2,5-dihydro-2H-pyrans is reported. Sonogashira coupling of 4-pentyn-l-ol and 5-hexyn-2-ol with a range of phenyl and naphthyl bromides affords the appropriate aryl acetylenic alcohols which then undergo ready reduction to the corresponding (E)-1-aryl-5-hydroxyalkenes. Subsequent selenoetherification of the (E)-5-hydroxyalkenes proceeds via a 6-endo-trig pathway cleanly affording the trans-2-aryl-3-phenylselenyltetrallydropyrans. Finally oxidative elimination of the selenides afforded the 2-aryl-2,5-dihydro-2H-pyrans which are convenient intermediates for the synthesis of C-aryl glycosides in that they contain a double bond which is available for further oxygenation. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1735 / 1738

页数：4

共 27 条

[1] RULES FOR RING-CLOSURE [J].