Transformations of lignans. Part 10: Acid-catalysed rearrangements of arboreol and wodeshiol and conversion of gmelanone oxime into a dihydropyranone derivative

被引：7
作者：
Venkateswarlu, R [1 ]
Kamakshi, C
Subhash, PV
Moinuddin, SGA
Gowri, MP
Ward, RS
Pelter, A
Hursthouse, MB
Coles, SJ
Light, ME
机构：
[1] Andhra Univ, Dept Organ Chem, Waltair 530003, Andhra Pradesh, India
[2] Univ Coll Swansea, Dept Chem, Swansea SA2 8PP, W Glam, Wales
[3] Univ Southampton, Sch Chem, EPSRC Natl Crystallog Serv, Southampton SO17 1BJ, Hants, England
来源：
TETRAHEDRON | 2005年 / 61卷 / 37期
关键词：
lignans; pinacol rearrangement; biomimetic synthesis; oxime rearrangement;
D O I：
10.1016/j.tet.2005.06.106
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of gmelanone 2 by a pinacol-type rearrangement of arboreol I supports its biogenesis and confirms its relative and absolute configuration. The further transformation of gmelanone oxime 12 into the dihydropyranone oxime 13 supports the intermediacy of gmelanone like intermediates in the rearrangements of furofuran lignans to pyran derivatives. In contrast, acid-catalysed rearrangement of wodeshiol 7 affords the dihydropyranone 8. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8956 / 8961
页数：6
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