Formal synthesis of (+)-SCH 351448: the Prins cyclization approach

被引:60
作者
Chan, Kok-Ping [1 ]
Ling, Yvonne Hui [1 ]
Loh, Teck-Peng [1 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Singapore 637616, Singapore
关键词
D O I
10.1039/b616558c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The formal synthesis of (+)-SCH 351448 has been accomplished with the catalytic Prins cyclization strategy, yielding the monomeric unit as a single isomer.
引用
收藏
页码:939 / 941
页数:3
相关论文
共 32 条
[11]   Cross-metathesis reaction. Generation of highly functionalized olefins from unsaturated alcohols (vol 624, pg 327, 2001) [J].
Cossy, J ;
BouzBouz, S ;
Hoveyda, AH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 634 (02) :215-221
[12]   Enantioselective total synthesis of (+)-SCH 351448 [J].
Crimmins, Michael T. ;
Vanier, Grace S. .
ORGANIC LETTERS, 2006, 8 (13) :2887-2890
[13]   Synthesis of 2-Hydroxy-6-{[(16R)-beta-D-mannopyranosyloxy]heptadecyl}benzoic acid, a fungal metabolite with GABA(A) ion channel receptor inhibiting properties [J].
Furstner, A ;
Konetzki, I .
TETRAHEDRON, 1996, 52 (48) :15071-15078
[14]   A novel microbial metabolite, activator of low density lipoprotein receptor promoter [J].
Hegde, VR ;
Puar, MS ;
Dai, P ;
Patel, M ;
Gullo, VP ;
Das, PR ;
Bond, RW ;
McPhail, AT .
TETRAHEDRON LETTERS, 2000, 41 (09) :1351-1354
[15]   CHIRAL SYNTHESIS VIA ORGANOBORANES .5. ASYMMETRIC ALLYLBORATION VIA CHIRAL ALLYLDIALKYLBORANES - SYNTHESIS OF HOMOALLYLIC ALCOHOLS WITH EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS [J].
JADHAV, PK ;
BHAT, KS ;
PERUMAL, PT ;
BROWN, HC .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (04) :432-439
[16]   Racemization in prins cyclization reactions [J].
Jasti, Ramesh ;
Rychnovsky, Scott D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (41) :13640-13648
[17]   Total synthesis of (+)-SCH 351448 [J].
Kang, EJ ;
Cho, EJ ;
Lee, YE ;
Ji, MK ;
Shin, DM ;
Chung, YK ;
Lee, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2680-2681
[18]  
Lipshutz BH, 1989, SYNLETT, P64
[19]   Indium trichloride catalysed Mukaiyama aldol reaction in water [J].
Loh, TP ;
Pei, JA ;
Cao, GQ .
CHEMICAL COMMUNICATIONS, 1996, (15) :1819-1820
[20]   Highly enantioselective allylation of aldehydes catalyzed by indium(III)-PYBOX complex [J].
Lu, J ;
Ji, SJ ;
Teo, YC ;
Loh, TP .
ORGANIC LETTERS, 2005, 7 (01) :159-161