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The total synthesis of (+)-tedanolide
被引:50
作者
:
Ehrlich, Gunnar
论文数:
0
引用数:
0
h-index:
0
机构:
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Ehrlich, Gunnar
[
1
]
Hassfeld, Jorma
论文数:
0
引用数:
0
h-index:
0
机构:
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Hassfeld, Jorma
[
1
]
Eggert, Ulrike
论文数:
0
引用数:
0
h-index:
0
机构:
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Eggert, Ulrike
[
1
]
Kalesse, Markus
论文数:
0
引用数:
0
h-index:
0
机构:
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
Kalesse, Markus
[
1
]
机构
:
[1]
Leibniz Univ Hannover, Inst Organ Chem, D-30167 Hannover, Germany
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2006年
/ 128卷
/ 43期
关键词
:
D O I
:
10.1021/ja0659572
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide. Copyright © 2006 American Chemical Society.
引用
收藏
页码:14038 / 14039
页数:2
相关论文
共 42 条
[11]
JULIAN LD, 2005, THESIS U MICHIGAN
[12]
Efficient synthesis of the C1-C11 fragment of the tedanolides.: The nonaldol aldol process in synthesis
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Marquez, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Marquez, R
[J].
ORGANIC LETTERS,
2000,
2
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: 1669
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1672
[13]
Conversion of homoallylic alcohols with alkene protection to the corresponding methyl ketones
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Karama, U
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Karama, U
Marquez, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Marquez, R
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1999,
64
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665
[14]
Rearrangement of epoxides in non-aldol aldol process: Allylic vs. tertiary and secondary carbocationic centers
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Marquez, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Marquez, R
[J].
TETRAHEDRON LETTERS,
1999,
40
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: 3129
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3132
[15]
Synthesis of a fully functionalized protected C1-C11 fragment for the synthesis of the tedanolides
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Lee, CP
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Lee, CP
[J].
ORGANIC LETTERS,
2001,
3
(03)
: 333
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336
[16]
1,1,1,3,3,3-HEXAFLUORO-2-PROPANOL FOR THE REMOVAL OF THE 4,4'-DIMETHOXYTRITYL PROTECTING GROUP FROM THE 5'-HYDROXYL OF ACID-SENSITIVE NUCLEOSIDES AND NUCLEOTIDES
LEONARD, NJ
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
LEONARD, NJ
NEELIMA
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
NEELIMA
[J].
TETRAHEDRON LETTERS,
1995,
36
(43)
: 7833
-
7836
[17]
LEY SV, 1994, SYNTHESIS-STUTTGART, P639
[18]
Attainment of syn-selectivity for boron-mediated asymmetric aldol reactions of carboxylic esters
Liu, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Liu, JF
Abiko, A
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Abiko, A
Pei, ZH
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Pei, ZH
Buske, DC
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Buske, DC
论文数:
引用数:
h-index:
机构:
Masamune, S
[J].
TETRAHEDRON LETTERS,
1998,
39
(14)
: 1873
-
1876
[19]
Synthetic studies towards the total synthesis of tedanolide: formation of the C(13)-C(23) fragment
Loh, TP
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Loh, TP
Feng, LC
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Feng, LC
[J].
TETRAHEDRON LETTERS,
2001,
42
(18)
: 3223
-
3226
[20]
Progress towards the total synthesis of tedanolide:: an efficient assembly of the C1-C11 subunit
Loh, TP
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Loh, TP
Feng, LC
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Feng, LC
[J].
TETRAHEDRON LETTERS,
2001,
42
(34)
: 6001
-
6005
←
1
2
3
4
5
→
共 42 条
[11]
JULIAN LD, 2005, THESIS U MICHIGAN
[12]
Efficient synthesis of the C1-C11 fragment of the tedanolides.: The nonaldol aldol process in synthesis
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Marquez, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Marquez, R
[J].
ORGANIC LETTERS,
2000,
2
(12)
: 1669
-
1672
[13]
Conversion of homoallylic alcohols with alkene protection to the corresponding methyl ketones
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Karama, U
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Karama, U
Marquez, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Marquez, R
[J].
JOURNAL OF ORGANIC CHEMISTRY,
1999,
64
(02)
: 663
-
665
[14]
Rearrangement of epoxides in non-aldol aldol process: Allylic vs. tertiary and secondary carbocationic centers
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Marquez, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Marquez, R
[J].
TETRAHEDRON LETTERS,
1999,
40
(16)
: 3129
-
3132
[15]
Synthesis of a fully functionalized protected C1-C11 fragment for the synthesis of the tedanolides
Jung, ME
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Jung, ME
Lee, CP
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Lee, CP
[J].
ORGANIC LETTERS,
2001,
3
(03)
: 333
-
336
[16]
1,1,1,3,3,3-HEXAFLUORO-2-PROPANOL FOR THE REMOVAL OF THE 4,4'-DIMETHOXYTRITYL PROTECTING GROUP FROM THE 5'-HYDROXYL OF ACID-SENSITIVE NUCLEOSIDES AND NUCLEOTIDES
LEONARD, NJ
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
LEONARD, NJ
NEELIMA
论文数:
0
引用数:
0
h-index:
0
机构:
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
UNIV ILLINOIS,SCH CHEM SCI,ROGER ADAMS LAB,URBANA,IL 61801
NEELIMA
[J].
TETRAHEDRON LETTERS,
1995,
36
(43)
: 7833
-
7836
[17]
LEY SV, 1994, SYNTHESIS-STUTTGART, P639
[18]
Attainment of syn-selectivity for boron-mediated asymmetric aldol reactions of carboxylic esters
Liu, JF
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Liu, JF
Abiko, A
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Abiko, A
Pei, ZH
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Pei, ZH
Buske, DC
论文数:
0
引用数:
0
h-index:
0
机构:
Kyoto Inst Technol, Venture Lab, Sakyo Ku, Kyoto 606, Japan
Buske, DC
论文数:
引用数:
h-index:
机构:
Masamune, S
[J].
TETRAHEDRON LETTERS,
1998,
39
(14)
: 1873
-
1876
[19]
Synthetic studies towards the total synthesis of tedanolide: formation of the C(13)-C(23) fragment
Loh, TP
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Loh, TP
Feng, LC
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Feng, LC
[J].
TETRAHEDRON LETTERS,
2001,
42
(18)
: 3223
-
3226
[20]
Progress towards the total synthesis of tedanolide:: an efficient assembly of the C1-C11 subunit
Loh, TP
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Loh, TP
Feng, LC
论文数:
0
引用数:
0
h-index:
0
机构:
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
Feng, LC
[J].
TETRAHEDRON LETTERS,
2001,
42
(34)
: 6001
-
6005
←
1
2
3
4
5
→