SYNTHESIS OF THE C(3)-C(15) SEGMENT OF RUTAMYCIN-B VIA A C(8)-C(9) FRAGMENT ASSEMBLY ALDOL REACTION - METAL DEPENDENCE OF THE ALDEHYDE AND ENOLATE DIASTEREOFACIAL SELECTIVITIES

被引：20

作者：

GUSTIN, DJ ^{[1
]}

VANNIEUWENHZE, MS ^{[1
]}

ROUSH, WR ^{[1
]}

机构：

[1] INDIANA UNIV,DEPT CHEM,BLOOMINGTON,IN 47405

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 20期

关键词：

D O I：

10.1016/0040-4039(95)00628-P

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereofacial selectivities of aldehyde 2b and ketone 3 are metal dependent, and their fragment assembly aldol coupling is a matched double asymmetric reaction when a chlorortitanium enolate is used.

引用

页码：3447 / 3450

页数：4

共 21 条

[1] X-RAY STRUCTURE OF ANTIBIOTIC RUTAMYCIN
ARNOUX, B
GARCIAALVAREZ, MC
MARAZANO, C
DAS, BC
PASCARD, C
MERIENNE, C
STARON, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (07) : 318 - 319
[2] STUDIES DIRECTED TOWARD THE SYNTHESIS OF THE RUTAMYCINS - ASSEMBLAGE OF THE POLYPROPIONATE REGION OF RUTAMYCIN-B
EVANS, DA
NG, HP
[J]. TETRAHEDRON LETTERS, 1993, 34 (14) : 2229 - 2232
[3] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC RUTAMYCIN-B
EVANS, DA
NG, HP
RIEGER, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) : 11446 - 11459
[4] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES
EVANS, DA
VOGEL, E
NELSON, JV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (20) : 6120 - 6123
[5] STEREOSELECTIVE ALDOL REACTIONS OF CHLOROTITANIUM ENOLATES - AN EFFICIENT METHOD FOR THE ASSEMBLAGE OF POLYPROPIONATE-RELATED SYNTHONS
EVANS, DA
RIEGER, DL
BILODEAU, MT
URPI, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) : 1047 - 1049
[6] EVANS DA, 1982, TOP STEREOCHEM, V13, P1, DOI DOI 10.1002/9780470147221.CHL
[7] DIASTEREOFACIAL SELECTIVITY IN THE ALDOL REACTIONS OF CHIRAL ALPHA-METHYL ALDEHYDES - A COMPUTER MODELING APPROACH
GENNARI, C
VIETH, S
COMOTTI, A
VULPETTI, A
GOODMAN, JM
PATERSON, I
[J]. TETRAHEDRON, 1992, 48 (21) : 4439 - 4458
[8] DIMETHYLBORON BROMIDE AND DIPHENYLBORON BROMIDE - CLEAVAGE OF ACETALS AND KETALS
GUINDON, Y
YOAKIM, C
MORTON, HE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) : 3912 - 3920
[9] DIASTEREOSELECTIVE ALDOL REACTIONS OF CHIRAL ALDEHYDES AND CHIRAL METHYL KETONES - DEPENDENCE OF STEREOSELECTIVITY ON THE METAL ENOLATE, THE ALDEHYDE 2,3-STEREOCHEMISTRY, AND THE ALDEHYDE BETA-ALKOXY PROTECTING GROUP
GUSTIN, DJ
VANNIEUWENHZE, MS
ROUSH, WR
[J]. TETRAHEDRON LETTERS, 1995, 36 (20) : 3443 - 3446
[10] CHEMISTRY OF CARBANIONS .23. USE OF METAL-COMPLEXES TO CONTROL ALDOL CONDENSATION
HOUSE, HO
CRUMRINE, DS
TERANISH.AY
OLMSTEAD, HD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (10) : 3310 - 3324

← 1 2 3 →