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The total synthesis of (-)-lemonomycin
被引:73
作者
:
Ashley, ER
论文数:
0
引用数:
0
h-index:
0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Ashley, ER
[
1
]
Cruz, EG
论文数:
0
引用数:
0
h-index:
0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Cruz, EG
[
1
]
Stoltz, BM
论文数:
0
引用数:
0
h-index:
0
机构:
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
Stoltz, BM
[
1
]
机构
:
[1]
CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2003年
/ 125卷
/ 49期
关键词
:
D O I
:
10.1021/ja039223q
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The first total synthesis of the novel glycosylated tetrahydroisoquinoline antitumor antibiotic (?)-lemonomycin has been accomplished (15 steps from 9). The highly convergent synthesis relies on a key asymmetric dipolar cycloaddition to set the stereochemistry of the aglycone core, a Suzuki fragment coupling to connect the diazabicycle to the aryl subunit, and a stereoselective Pictet?Spengler reaction that incorporates the aminoglycoside subunit directly into the core structure without the need for late-stage glycosylation or protecting group manipulations. The novel aminoglycoside was prepared using a highly diastereoselective Felkin-controlled acetate aldol addition reaction to a threonine-derived ketone. Copyright © 2003 American Chemical Society.
引用
收藏
页码:15000 / 15001
页数:2
相关论文
共 13 条
[11]
Total synthesis of (-)-tetrazomine. Determination of the stereochemistry of tetrazomine and the synthesis and biological activity of tetrazomine analogues
Scott, JD
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Scott, JD
Williams, RM
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Williams, RM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(12)
: 2951
-
2956
[12]
WHALEY H A, 1964, Antimicrob Agents Chemother (Bethesda), V14, P83
[13]
YATES ND, 1995, HETEROCYCLES, V40, P331
←
1
2
→
共 13 条
[11]
Total synthesis of (-)-tetrazomine. Determination of the stereochemistry of tetrazomine and the synthesis and biological activity of tetrazomine analogues
Scott, JD
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Scott, JD
Williams, RM
论文数:
0
引用数:
0
h-index:
0
机构:
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
Williams, RM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2002,
124
(12)
: 2951
-
2956
[12]
WHALEY H A, 1964, Antimicrob Agents Chemother (Bethesda), V14, P83
[13]
YATES ND, 1995, HETEROCYCLES, V40, P331
←
1
2
→