Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: Total syntheses of 1,4-dideoxy-1,4-imino-d-arabinitol and (-)-lentiginosine

被引:51
作者
Kim, In Su [1 ]
Zee, Ok Pyo [1 ]
Jung, Young Hoon [1 ]
机构
[1] Sungkyunkwan Univ, Coll Pharm, Suwon 440746, South Korea
关键词
D O I
10.1021/ol061614x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total syntheses of DAB1 (1) and (-)-lentiginosine (2) were concisely accomplished from D-lyxose via regioselective and diastereoselective NHCbz introduction using CSI, chemoselective removal of the Cbz protection, and ring-closing metathesis as key steps.
引用
收藏
页码:4101 / 4104
页数:4
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共 60 条
[1]   ROLE OF NEIGHBORING GROUPS IN REPLACEMENT REACTIONS .27. 5-METHOXYL PARTICIPATION IN SOME SOLVOLYSIS REACTIONS [J].
ALLRED, EL ;
WINSTEIN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (16) :3991-&
[2]   5-METHOXYL PARTICIPATION IN ACETOLYSIS . ION AND ION-PAIR INTERMEDIATES [J].
ALLRED, EL ;
WINSTEIN, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (16) :3998-&
[3]   STEREOSELECTIVE SYNTHESIS OF SUBSTITUTED PIPECOLIC ACIDS [J].
ANGLE, SR ;
ARNAIZ, DO .
TETRAHEDRON LETTERS, 1989, 30 (05) :515-518
[4]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[5]   Concise asymmetric syntheses of (-)-lentiginosine and of its pyrrolizidinic analogue [J].
Ayad, T ;
Génisson, Y ;
Baltas, M ;
Gorrichon, L .
CHEMICAL COMMUNICATIONS, 2003, (05) :582-583
[6]   ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF NATURAL LENTIGINOSINE BY SYNTHESIS AND ENZYMATIC ASSAYS OF OPTICALLY PURE (+)-ENANTIOMERS AND (-)-ENANTIOMERS [J].
BRANDI, A ;
CICCHI, S ;
CORDERO, FM ;
FRIGNOLI, R ;
GOTI, A ;
PICASSO, S ;
VOGEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) :6806-6812
[7]   New concise total synthesis of (+)-lentiginosine and some structural analogues [J].
Cardona, F ;
Moreno, G ;
Guarna, F ;
Vogel, P ;
Schuetz, C ;
Merino, P ;
Goti, A .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) :6552-6555
[8]   Total synthesis of (-)- and (+)-lentiginosine [J].
Chandra, KL ;
Chandrasekhar, M ;
Singh, VK .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4630-4633
[9]   (Z)-(E) INTERCONVERSION OF OLEFINS BY THE ADDITION-ELIMINATION SEQUENCE OF THE (TMS)(3)SI. RADICAL [J].
CHATGILIALOGLU, C ;
BALLESTRI, M ;
FERRERI, C ;
VECCHI, D .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3826-3831
[10]   SYNTHESIS OF LENTIGINOSINE BY STEREOSELECTIVE CHIRAL NITRONE CYCLOADDITION AND THERMAL REARRANGEMENT OF STRAINED SPIROISOXAZOLIDINE [J].
CORDERO, FM ;
CICCHI, S ;
GOTI, A ;
BRANDI, A .
TETRAHEDRON LETTERS, 1994, 35 (06) :949-952