Studies directed towards the total synthesis of (+)-himbacine

被引：29
|
作者：
Hofman, S [1 ]
De Baecke, G [1 ]
Kenda, B [1 ]
De Clercq, PJ [1 ]
机构：
[1] State Univ Ghent, Dept Organ Chem, Organ Synth Lab, B-9000 Ghent, Belgium
来源：
SYNTHESIS-STUTTGART | 1998年
关键词：
himbacine; intramolecular Diels-Alder reaction; butenolides; Julia coupling; 2,6-trans-disubstituted piperidines;
D O I：
10.1055/s-1998-5928
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.
引用
收藏
页码：479 / 489
页数：11
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