Diastereoselective synthesis endo- and exo-spirotetronate of the quartromicins.: The first enantioselective Diels-Alder reaction of an acyclic (Z)-1,3-diene

被引:44
作者
Roush, WR [1 ]
Limberakis, C [1 ]
Kunz, RK [1 ]
Barda, DA [1 ]
机构
[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA
关键词
D O I
10.1021/ol025772+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diastereoselective syntheses of the endo- and exo-spirotetronates 1 and 2, corresponding to the galacto and agalacto fragments of quartromicins A(3) and D-3, are described. The key step of these syntheses are highly enantio- and diastereoselective Lewis acid catalyzed Diels-Alder reactions of the 1,1,3,4-tetrasubstituted diene 3.
引用
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页码:1543 / 1546
页数:4
相关论文
共 21 条
[1]   KMNO4 REVISITED - OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS IN THE TERT-BUTYL ALCOHOL AQUEOUS NAH2PO4 SYSTEM [J].
ABIKO, A ;
ROBERTS, JC ;
TAKEMASA, T ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1986, 27 (38) :4537-4540
[2]   CHARACTERIZATION OF 2-SILOXYOXIRANES FORMED BY EPOXIDATION OF SILYL ENOL ETHERS WITH DIMETHYLDIOXIRANE [J].
CHENAULT, HK ;
DANISHEFSKY, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4249-4250
[3]  
De Lucchi O., 1991, ORG REACTIONS, V40, P157, DOI DOI 10.1002/0471264180.0R040.03
[4]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[5]   SCANDIUM TRIFLUOROMETHANESULFONATE AS AN EXTREMELY ACTIVE ACYLATION CATALYST [J].
ISHIHARA, K ;
KUBOTA, M ;
KURIHARA, H ;
YAMAMOTO, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) :4413-4414
[6]   THE STRUCTURES OF QUARTROMICIN-A1, QUARTROMICIN-A2, AND QUARTROMICIN-A3 - NOVEL MACROCYCLIC ANTIVIRAL ANTIBIOTICS POSSESSING 4 TETRONIC ACID MOIETIES [J].
KUSUMI, T ;
ICHIKAWA, A ;
KAKISAWA, H ;
TSUNAKAWA, M ;
KONISHI, M ;
OKI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8947-8948
[7]   AN ENANTIOSELECTIVE SYNTHESIS OF THE SPIROTETRONATE SUBUNIT OF KIJANOLIDE [J].
MARSHALL, JA ;
XIE, SP .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (11) :2987-2989
[8]  
OLAH GA, 1979, SYNTHESIS-STUTTGART, P720
[9]   ASYMMETRIC DIELS-ALDER REACTIONS - X-RAY CRYSTAL-STRUCTURE ANALYSIS OF [N-((E)-BUT-2-ENOYL)BORNANE-10,2-SULTAM]TETRACHLOROTITANIUM [J].
OPPOLZER, W ;
RODRIGUEZ, I ;
BLAGG, J ;
BERNARDINELLI, G .
HELVETICA CHIMICA ACTA, 1989, 72 (01) :123-130
[10]   CAMPHOR-DERIVED N-ACRYLOYL AND N-CROTONOYL SULTAMS - PRACTICAL ACTIVATED DIENOPHILES IN ASYMMETRIC DIELS-ALDER REACTIONS [J].
OPPOLZER, W ;
CHAPUIS, C ;
BERNARDINELLI, G .
HELVETICA CHIMICA ACTA, 1984, 67 (05) :1397-1401