SYNTHESIS OF SOME BIOACTIVE ACETYLENIC ALCOHOLS, COMPONENTS OF THE MARINE SPONGE CRIBROCHALINA-VASCULUM

被引：26

作者：

KULKARNI, BA ^{[1
]}

CHATTOPADHYAY, S ^{[1
]}

CHATTOPADHYAY, A ^{[1
]}

MAMDAPUR, VR ^{[1
]}

机构：

[1] BHABHA ATOM RES CTR,DIV BIOORGAN,MODULAR LAB,BOMBAY 400085,INDIA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 22期

关键词：

D O I：

10.1021/jo00074a022

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Grignard coupling of isopropylmagnesium bromide with 4-(tetrahydropyranyloxy)bromobutane (2) and subsequent bromination gave 4. Alkylation of 1-(tetrahydropyranyloxy)undec-10-yne (5) with 4 and 1-bromohexane, acidic hydrolysis, and bromination furnished 7 and 9, respectively. Likewise, coupling of isobutylmagnesium bromide with 12-(tetrahydropyranyloxy)bromododecane (12) followed by bromination afforded 14. Alkylation of 1-(tetrahydropyranyloxy)-2-propyne (15) with 7, 9, and 14 and oxidation of the respective products afforded the alkynals 16a-c. These on reaction with lithium acetylide and subsequent chemoselective trans reduction of the internal alkynes led to the target compounds I-III.

引用

页码：5964 / 5966

页数：3

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