An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A

被引：62
作者：
Gallos, JK [1 ]
Stathakis, CI [1 ]
Kotoulas, SS [1 ]
Koumbis, AE [1 ]
机构：
[1] Aristotle Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 17期
关键词：
D O I：
10.1021/jo050987t
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.
引用
收藏
页码：6884 / 6890
页数：7
相关论文
共 102 条
[1]  
ALI SM, 1990, TETRAHEDRON LETT, V31, P1509
[2]   Concise synthesis of (4S,5S)-4,5-(isopropylidenedioxy)-2-cyclopentenone and a novel C-2-symmetric ketone [J].
Armstrong, A ;
Hayter, BR .
TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1677-1684
[3]   AN ASYMMETRIC-SYNTHESIS OF (-)-CARBOVIR [J].
ASAMI, M ;
TAKAHASHI, J ;
INOUE, S .
TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1649-1652
[4]   (PHENYLTHIO)NITROMETHANE IN THE TOTAL SYNTHESIS OF POLYOXIN-C [J].
BARRETT, AGM ;
LEBOLD, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3853-3857
[5]   CARBOCYCLES FROM CARBOHYDRATES - A SIMPLE ROUTE TO AN ENANTIOMERICALLY PURE PROSTAGLANDIN INTERMEDIATE [J].
BELANGER, P ;
PRASIT, P .
TETRAHEDRON LETTERS, 1988, 29 (43) :5521-5524
[6]   CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .1. TRANSFORMATIONS IN THE GLUCOSE SERIES [J].
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1979, 62 (06) :1990-2016
[7]   CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .2. TRANSFORMATIONS IN THE MANNOSE SERIES [J].
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1979, 62 (07) :2400-2410
[8]   CARBOCYCLES FROM MONOSACCHARIDES .3. CONCERNING THE DIASTEREOSELECTIVE FORMATION OF CYCLOPENTANE DERIVATIVES - TRANSFORMATIONS IN THE GALACTOSE SERIES [J].
BERNET, B ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1979, 62 (07) :2411-2431
[9]   SYNTHESIS OF (-)-NEPLANOCIN A FROM (R,R)-TARTARIC ACID [J].
BESTMANN, HJ ;
ROTH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (01) :99-100
[10]   Chemoenzymatic synthesis of a versatile cyclopentenone: (+)-(3aS,6aS)-2,2-dimethyl-3a beta,6a beta-dihydro-4H-cyclopenta-1,3-dioxol-4-one [J].
Biadatti, T ;
Esker, JL ;
Johnson, CR .
TETRAHEDRON-ASYMMETRY, 1996, 7 (08) :2313-2320
12345678910