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

页码：479 / 489

页数：11

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