SYNTHESIS OF THE PSEUDOPTERANE AND FURANOCEMBRANE RING-SYSTEMS BY INTRAANNULAR CYCLIZATION OF BETA-ALKYNYL AND GAMMA-ALKYNYL ALLYLIC ALCOHOLS

被引:69
作者
MARSHALL, JA
DUBAY, WJ
机构
[1] Department of Chemistry and Biochemistry, University of South Carolina, Columbia
关键词
D O I
10.1021/jo00086a018
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The prototype pseudopterane and furanocembrane systems 15 and 26 were prepared through a ''furan last'' approach. The former was obtained in 64% yield upon treatment of the 12-membered beta-alkynyl allylic alcohol 14 with KO-t-Bu and 18-c-6 in THF-t-BuOH. The latter was formed in 88% yield from the 14-membered gamma-alkynyl allylic alcohol 25 under comparable conditions. The carbocyclic precursors to these allylic alcohols, 11 and 24, were secured through intramolecular Horner-Emmons condensation of keto phosphonates 10 and 23, respectively, under Masamune-Roush conditions.
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页码:1703 / 1708
页数:6
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