Enantioselective synthesis of the tricyclic core of (-)-FR901483

被引:22
作者
Asari, Asnuzilawati [1 ]
Angelov, Plamen [1 ]
Auty, James M. [1 ]
Hayes, Christopher J. [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/j.tetlet.2007.01.171
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantioselective synthesis of the tricyclic core structure of the immunosuppressant natural product (-)-FR901483 has been achieved. A palladium-catalysed (Pd-2(dba)(3), Xantphos, KOPh) intramolecular enolate alkenylation reaction was used as the key ring forming step for the construction of the bicyclo-[3,3,1]-azanonane ring system. An alkylidene carbene 1,5-CH insertion reaction was used to construct the nitrogen-bearing stereocentre in the vinyl bromide cyclisation precursor. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2631 / 2634
页数:4
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