ASYMMETRIC-SYNTHESIS OF (-)-DENTICULATIN-A AND (-)-DENTICULATIN-B VIA GROUP-SELECTIVE ALDOLIZATION OF A MESO DIALDEHYDE WITH A CHIRAL N-PROPIONYLSULTAM

被引:27
作者
OPPOLZER, W
DEBRABANDER, J
WALTHER, E
BERNARDINELLI, G
机构
[1] Départment de Chimie Organique, Université de Genève
关键词
D O I
10.1016/0040-4039(95)00787-D
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral N-propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers. Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is converted into the marine polypropionates 1a and 1b via the asymmetric alkylation of N-propionyltoluenesultam 11 and the aldol coupling 10 + 15 --> 16.
引用
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页码:4413 / 4416
页数:4
相关论文
共 25 条
  • [1] STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .38. STEREOSELECTIVE TOTAL SYNTHESIS OF THE DENTICULATINS
    ANDERSEN, MW
    HILDEBRANDT, B
    DAHMANN, G
    HOFFMANN, RW
    [J]. CHEMISCHE BERICHTE, 1991, 124 (09) : 2127 - 2139
  • [2] A SHORT, EFFICIENT SYNTHESIS OF (1S,3S,5R) AND (1S,3R,5R)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]-GNONANE
    BERNARDI, R
    GHIRINGHELLI, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) : 5021 - 5022
  • [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] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LONOMYCIN-A (EMERICID)
    EVANS, DA
    RATZ, AM
    HUFF, BE
    SHEPPARD, GS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) : 3448 - 3467
  • [5] FRANKLIN AS, 1994, CONTEMP ORG SYNTH, P317
  • [6] HEATHCOCK CH, 1991, COMPREHENSIVE ORGANI, V2, P181
  • [7] HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111
  • [8] THE DENTICULATINS, 2 POLYPROPIONATE METABOLITES FROM THE PULMONATE SIPHONARIA-DENTICULATA
    HOCHLOWSKI, JE
    FAULKNER, DJ
    MATSUMOTO, GK
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (25) : 7413 - 7415
  • [9] Hoffmann R. W., 1987, ANGEW CHEM, V99, P503
  • [10] HOFFMANN RW, 1994, SYNTHESIS-STUTTGART, P629