A FORMAL TOTAL SYNTHESIS OF 3-O-DEMETHYLFORTAMINE

被引：13

作者：

CAMBIE, RC ^{[1
]}

RENNER, ND ^{[1
]}

RUTLEDGE, PS ^{[1
]}

WOODGATE, PD ^{[1
]}

机构：

[1] UNIV AUCKLAND,DEPT CHEM,AUCKLAND,NEW ZEALAND

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1991年 / 44卷 / 01期

关键词：

D O I：

10.1071/CH9910061

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rho-Benzoquinone has been converted into the substituted cyclohexenone (11) in five steps and 33% overall yield by a Diels-Alder cycloaddition-cycloreversion approach in which anthracene functions as a protecting and stereodirecting group. The elaboration of (11) in four steps to the known epoxide (22) constitutes a formal total synthesis of 3-O-demethylfortamine (2).

引用

页码：61 / 75

页数：15

共 35 条

[21] KOMENO T, 1964, J ORG CHEM, V29, P1136
[22] TOTAL SYNTHESES OF (-)-2-DEOXYFORTAMINES
KUHLMEYER, R
SCHWESINGER, R
PRINZBACH, H
[J]. TETRAHEDRON LETTERS, 1984, 25 (32) : 3429 - 3432
[23] TOTAL SYNTHESIS OF FORTAMINE, THE AGLYCON OF THE MAJOR AMINOCYCLITOL ANTIBIOTICS FORTIMICIN-A AND FORTIMICIN-B
KUO, CH
WENDLER, NL
[J]. TETRAHEDRON LETTERS, 1984, 25 (22) : 2291 - 2294
[24] LANTHANIDES IN ORGANIC-CHEMISTRY .1. SELECTIVE 1,2 REDUCTIONS OF CONJUGATED KETONES
LUCHE, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (07) : 2226 - 2227
[25] MORAN GF, 1975, J ORG CHEM, V40, P184
[26] MORI Y, 1979, B CHEM SOC JPN, V52, P2727
[27] HIGHLY STEREOSELECTIVE SYNTHESIS OF ERYTHRO-ALPHA, BETA-EPOXY ALCOHOLS BY THE REDUCTION OF ALPHA, BETA-EPOXY KETONES WITH ZINC BOROHYDRIDE
NAKATA, T
TANAKA, T
OISHI, T
[J]. TETRAHEDRON LETTERS, 1981, 22 (47) : 4723 - 4726
[28] 2-SUBSTITUTED AND 2,6-DISUBSTITUTED 1,4-BENZOQUINONE 4-OXIMES (P-NITROSOPHENOLS)
NORRIS, RK
STERNHEL.S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (05) : 935 - &
[29] 2-SUBSTITUTED AND 2,6-DISUBSTITUTED 1,4-BENZOQUINONE 4-OXIME ACETATES
NORRIS, RK
STERNHEL.S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (07) : 1449 - &
[30] 2-SUBSTITUTED AND 2,6-DISUBSTITUTED 1,4-BENZOQUINONE 4-OXIME METHYL ETHERS
NORRIS, RK
STERNHEL.S
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1972, 25 (09) : 1907 - &

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