DIELS-ALDER REACTIONS OF CYCLOPROPENONE KETALS - A CONCISE TROPOLONE ANNULATION APPLICABLE TO RUBROLONE-C RING INTRODUCTION

被引：31

作者：

BOGER, DL

ZHU, Y

机构：

[1] Department of Chemistry, Scripps Research Institute, California 92037, 10666 North Torrey Pines Road, La Jolla

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 12期

关键词：

D O I：

10.1021/jo00091a040

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise tropolone annulation applicable to rubrolone C ring introduction is detailed based on the room-temperature [4 + 2] cycloaddition reaction of the cyclopropenone ketal 10 with the oxygenated diene 9. Conversion of the sensitive [4 + 2] cycloadduct 11 to the norcaradiene 18, low temperature electrocyclic rearrangement to a cycloheptatrienone ketal, and tautomerization to 12 provided a fully oxygenated tropolone analogous to that found in rubrolone.

引用

页码：3453 / 3458

页数：6

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