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

页码：6884 / 6890

页数：7

共 102 条

[41] Enantiospecific synthesis of (-)-5-epi-shikimic acid and (-)-shikimic acid [J].

Jiang, SD ;

McCullough, KJ ;

Mekki, B ;

Singh, G ;

Wightman, RH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12) :1805-1814

[42] ENANTIOSPECIFIC SYNTHESIS OF (-)-5-EPI-SHIKIMIC ACID AND A NEW ROUTE TO (-)-SHIKIMIC ACID [J].

JIANG, SD ;

MEKKI, B ;

SINGH, G ;

WIGHTMAN, RH .

TETRAHEDRON LETTERS, 1994, 35 (30) :5505-5508

[43] Practical synthesis of D- and L-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus) [J].

Jin, YH ;

Liu, P ;

Wang, JN ;

Baker, R ;

Huggins, J ;

Chu, CK .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :9012-9018

[44] SYNTHESIS OF PGE1 AND VARIOUS 10-ALPHA-HYDROXYPROSTAGLANDINS [J].

JOHNSON, CR ;

CHEN, YF .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3352-3357

[45] DEVELOPMENT OF A TRIPLY CONVERGENT ALDOL APPROACH TO PROSTANOIDS [J].

JOHNSON, CR ;

CHEN, YF .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3344-3351

[46] CHEMOENZYMATIC SYNTHESIS OF 1,3-DIDEOXYNOJIRIMYCIN [J].

JOHNSON, CR ;

GOLEBIOWSKI, A ;

BRAUN, MP ;

SUNDRAM, H .

TETRAHEDRON LETTERS, 1994, 35 (12) :1833-1834

[47]

JOHNSON CR, 1995, SYNLETT, P313

[48] CHEMOENZYMATIC SYNTHESIS OF TRANS-4,5-DIHYDROXYCYCLOPENT-2-ENONES - CONVERSION TO D-1-DEOXYNOJIRIMYCIN [J].

JOHNSON, CR ;

NERURKAR, BM ;

GOLEBIOWSKI, A ;

SUNDRAM, H ;

ESKER, JL .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (11) :1139-1140

[49] A 2-STEP, 3-COMPONENT SYNTHESIS OF PGE(1) - UTILIZATION OF ALPHA-IODOENONES IN PD(0)-CATALYZED CROSS-COUPLINGS OF ORGANOBORANES [J].

JOHNSON, CR ;

BRAUN, MP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) :11014-11015

[50] DIRECT ALPHA-IODINATION OF CYCLOALKENONES [J].

JOHNSON, CR ;

ADAMS, JP ;

BRAUN, MP ;

SENANAYAKE, CBW ;

WOVKULICH, PM ;

USKOKOVIC, MR .

TETRAHEDRON LETTERS, 1992, 33 (07) :917-918

← 1 2 3 4 5 6 7 8 9 10 →