A SYNTHESIS OF NATURALLY-OCCURRING (1S,2S,3R)-4-HYDROXYMETHYLCYCLOPENT-4-ENE-1,2,3-TRIOL UTILIZING THE CYCLIZATION OF A DIOXOLANYL RADICAL

被引:0
作者
ZIEGLER, FE
HARRAN, PG
机构
关键词
RADICAL; CYCLIZATION; CHIRAL; ARISTEROMYCIN; NEPLANOCIN A;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A radical cyclization is employed in the synthesis of a biosynthetic precursor of aristeromycin and neplanocin A. A derivative of L-tartaric acid is used as both the source of chirality and the carbon radical.
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页码:493 / 494
页数:2
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共 23 条
[1]   SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES [J].
AGROFOGLIO, L ;
SUHAS, E ;
FARESE, A ;
CONDOM, R ;
CHALLAND, SR ;
EARL, RA ;
GUEDJ, R .
TETRAHEDRON, 1994, 50 (36) :10611-10670
[2]   SYNTHESIS OF 2S, 3AS, 7AS-PERHYDROINDOLE-2-CARBOXYLIC AND OF 2S, 3AR, 7AR-PERHYDROINDOLE-2-CARBOXYLIC ACID-DERIVATIVES FROM L-ASPARTIC ACID [J].
BARTON, DHR ;
GUILHEM, J ;
HERVE, Y ;
POTIER, P ;
THIERRY, J .
TETRAHEDRON LETTERS, 1987, 28 (13) :1413-1416
[3]   THE INVENTION OF RADICAL REACTIONS .25. A CONVENIENT METHOD FOR THE SYNTHESIS OF THE ACYL DERIVATIVES OF N-HYDROXYPYRIDINE-2-THIONE [J].
BARTON, DHR ;
SAMADI, M .
TETRAHEDRON, 1992, 48 (35) :7083-7090
[4]   THE INVENTION OF NEW RADICAL CHAIN-REACTIONS .9. FURTHER RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - FORMATION OF CARBON CARBON BONDS [J].
BARTON, DHR ;
CRICH, D ;
KRETZSCHMAR, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (01) :39-53
[5]   THE INVENTION OF NEW RADICAL CHAIN REACTIONS .8. RADICAL CHEMISTRY OF THIOHYDROXAMIC ESTERS - A NEW METHOD FOR THE GENERATION OF CARBON RADICALS FROM CARBOXYLIC-ACIDS [J].
BARTON, DHR ;
CRICH, D ;
MOTHERWELL, WB .
TETRAHEDRON, 1985, 41 (19) :3901-3924
[6]   RATE CONSTANTS AND ARRHENIUS PARAMETERS FOR THE REACTIONS OF PRIMARY, SECONDARY, AND TERTIARY ALKYL RADICALS WITH TRI-NORMAL-BUTYLTIN HYDRIDE [J].
CHATGILIALOGLU, C ;
INGOLD, KU ;
SCAIANO, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (26) :7739-7742
[7]   ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS [J].
CHATGILIALOGLU, C .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) :188-194
[8]   ASYMMETRIC DIHYDROXYLATIONS VIA CHIRAL OXAZOLIDINES [J].
COLOMBO, L ;
GENNARI, C ;
POLI, G ;
SCOLASTICO, C ;
DEMUNARI, S .
TETRAHEDRON LETTERS, 1985, 26 (44) :5459-5462
[9]   SILANES IN ORGANIC-SYNTHESIS .11. REGIOCONTROLLED SYNTHESIS OF ALPHA-HYDROXYMETHYLATED (TRIMETHYLSILYL)ALLENES [J].
DANIELS, RG ;
PAQUETTE, LA .
TETRAHEDRON LETTERS, 1981, 22 (17) :1579-1582
[10]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287