Chemoenzymatic synthesis of deoxy analogues of the DNA topoisomerase II inhibitor eleutherin and the 3C-protease inhibitor thysanone

被引:24
作者
Bachu, Prabhakar [1 ]
Sperry, Jonathan [1 ]
Brimble, Margaret A. [1 ]
机构
[1] Univ Auckland, Dept Chem, Auckland 1, New Zealand
关键词
eleutherin; thysanone; topoisomerase II inhibitor; 3C-protease inhibitor; Novozyme 4350 (Candida antarctica lipase); microwave assisted lipase kinetic resolution; intramolecular cyclization;
D O I
10.1016/j.tet.2008.01.112
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric synthesis of (-)-9-demethoxyeleutherin 6, (+)-9-demethoxyeleutherin 7 and (+)-7,9-deoxythysanone 8 has been achieved using a microwave assisted kinetic resolution of racemic alcohol 11 with Novozyme 435 (R) as the key step. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4827 / 4834
页数:8
相关论文
共 43 条
[1]   The influence of microwave irradiation on lipase-catalyzed kinetic resolution of racemic secondary alcohols [J].
Bachu, Prabhakar ;
Gibson, Jennifer S. ;
Sperry, Jonathan ;
Brimble, Margaret A. .
TETRAHEDRON-ASYMMETRY, 2007, 18 (13) :1618-1624
[2]   Asymmetric Michael addition of 2-trimethylsilyloxyfuran to chiral naphthoquinones [J].
Brimble, MA ;
McEwan, JF ;
Turner, P .
TETRAHEDRON-ASYMMETRY, 1998, 9 (07) :1257-1267
[3]   Addition of 2-tert-butyldimethylsilyloxythiophene to activated quinones:: an approach to thia analogues of kalafungin [J].
Brimble, MA ;
Laita, O ;
Robinson, JE .
TETRAHEDRON, 2006, 62 (13) :3021-3027
[4]   Synthesis of regioisomeric analogues of crisamicin A [J].
Brimble, MA ;
Lai, MYH .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (23) :4227-4234
[5]   Synthesis of a dimeric pyranonaphthoquinone via a novel double furofuran annulation strategy [J].
Brimble, MA ;
Neville, D ;
Duncalf, LJ .
TETRAHEDRON LETTERS, 1998, 39 (31) :5647-5650
[6]   Double furofuran annulation to a bis-naphthoquinone: an approach to dimeric pyranonaphthoquinones [J].
Brimble, MA ;
Duncalf, LJ ;
Neville, D .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (24) :4165-4173
[7]   Synthesis of 3-azido-2,3,6-trideoxy-β-D-arabino-hexopyranosyl pyranonaphthoquinone analogues of medermycin [J].
Brimble, MA ;
Davey, RM ;
McLeod, MD ;
Murphy, M .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (10) :1690-1700
[8]   Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone [J].
Brimble, MA ;
Elliott, RJR .
TETRAHEDRON, 2002, 58 (01) :183-189
[9]   Synthesis of azido analogues of medermycin [J].
Brimble, MA ;
Davey, RM ;
McLeod, MD .
SYNLETT, 2002, (08) :1318-1322
[10]   Synthesis of a 2-deoxyglucosyl analogue of medermycin [J].
Brimble, MA ;
Brenstrum, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14) :1624-1634