DIASTEREOFACE SELECTIVITY IN RADICAL-MEDIATED C-C BOND FORMATION OF URIDINE 5'-MONOSELENOACETALS

被引：10

作者：

HARAGUCHI, K ^{[1
]}

TANAKA, H ^{[1
]}

SAITO, S ^{[1
]}

YAMAGUCHI, K ^{[1
]}

MIYASAKA, T ^{[1
]}

机构：

[1] SHOWA UNIV,SCH PHARMACEUT SCI,SHINAGAWA KU,TOKYO 142,JAPAN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 52期

关键词：

RADICAL REACTION; CRAMS RULE; URIDINE; MONOSELENOACETAL; DIASTEREOSELECTIVITY;

D O I：

10.1016/0040-4039(94)88369-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular radical reaction of 2'3'-O-isopropylideneuridine 5'-monoselenoacetal 6 appeared to result in reverse stereoselectivity to that of the corresponding 5'-aldehyde (3). Intermolecular version of this reaction by using allyltributylstannane as a radical acceptor showed preferential anti-Cram diastereoface selection.

引用

页码：9721 / 9724

页数：4

共 12 条

[1] ALDOL REACTION OF NUCLEOSIDE 5'-CARBOXALDEHYDES WITH ACETONE - SYNTHESIS OF 5'-C-CHAIN EXTENDED THYMIDINE DERIVATIVES [J].

CAMARASA, MJ ;

DELASHERAS, FG ;

PEREZPEREZ, MJ .

NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (04) :533-546

[2] ON THE COMMUNICATION OF CHIRALITY FROM FURANOSE AND PYRANOSE RINGS TO MONOSACCHARIDE SIDE-CHAINS - ANOMALOUS RESULTS IN THE GLUCOSE SERIES [J].

DANISHEFSKY, SJ ;

DENINNO, MP ;

PHILLIPS, GB ;

ZELLE, RE ;

LARTEY, PA .

TETRAHEDRON, 1986, 42 (11) :2809-2819

[3] CRAM'S RULE FOR RADICAL REACTIONS [J].

GIESE, B ;

DAMM, W ;

DICKHAUT, J ;

WETTERICH, F ;

SUN, SN ;

CURRAN, DP .

TETRAHEDRON LETTERS, 1991, 32 (43) :6097-6100

[4] STEREOCONTROLLED ACCESS TO THE OCTOSYL ACIDS - TOTAL SYNTHESIS OF OCTOSYL ACID-A [J].

HANESSIAN, S ;

KLOSS, J ;

SUGAWARA, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) :2758-2759

[5] PUMMERER REARRANGEMENT OF SELENIUM-CONTAINING URACIL NUCLEOSIDES [J].

HARAGUCHI, K ;

SAITO, S ;

TANAKA, H ;

MIYASAKA, T .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (2-4) :483-493

[6] DIRECT FREE-RADICAL SUBSTITUTIONS ON ALLYL AND VINYL HALIDES USING ALKYL-HALIDES HEXABUTYLDITIN [J].

HUVAL, CC ;

SINGLETON, DA .

TETRAHEDRON LETTERS, 1993, 34 (19) :3041-3042

[7] REVISED METHOD FOR CALCULATION OF GROUP ELECTRONEGATIVITIES [J].

INAMOTO, N ;

MASUDA, S .

CHEMISTRY LETTERS, 1982, (07) :1003-1006

[8] A CONVERGENT SYNTHETIC ROUTE TO THE TUNICAMYCIN ANTIBIOTICS - SYNTHESIS OF (+)-TUNICAMYCIN-V [J].

MYERS, AG ;

GIN, DY ;

ROGERS, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (05) :2036-2038

[9] ACYCLIC STEREOCHEMICAL CONTROL IN FREE-RADICAL REACTIONS [J].

PORTER, NA ;

GIESE, B ;

CURRAN, DP .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) :296-304

[10] NUCLEOSIDES .76. SYNTHESIS OF A CARBON-CARBON BRIDGED PYRIMIDINE CYCLONUCLEOSIDE [J].

RABI, JA ;

FOX, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (24) :3898-&

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