Studies in marine macrolide synthesis:: Stereocontrolled synthesis of the C1-C11 and C15-C27 subunits of aplyronine A

被引:29
作者
Paterson, I [1 ]
Cowden, CJ [1 ]
Woodrow, MD [1 ]
机构
[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England
关键词
D O I
10.1016/S0040-4039(98)01191-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aplyronine C-1-C-11 subunit 4, containing 4 stereocentres and the (E,E)-diene system, was prepared in 7 steps from ethyl ketone (R)-8 using a boron-mediated anti aldol reaction. The corresponding C-15-C-27 subunit 5, containing 6 stereogenic centres and an (E)-alkene, was obtained in 10 steps from ketone (S)-14 using a tin(II)-mediated syn aldol reaction and CBS enone reduction. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6037 / 6040
页数:4
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