TOTAL SYNTHESIS OF QUASSINOIDS AND VIRGINIAMYCIN
苦木素和维吉尼亚霉素的全合成
基本信息
- 批准号:3279193
- 负责人:
- 金额:$ 12.78万
- 依托单位:
- 依托单位国家:美国
- 项目类别:
- 财政年份:1979
- 资助国家:美国
- 起止时间:1979-04-01 至 1988-03-31
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
A total synthesis of the highly cytotoxic pentacyclic diterpene,
quasimarian is proposed. Starting from D-(+)-glucose, we intend to prepare
a monocyclic alpha-methylene-3-oxycyclopentanone which contains a total of
three chiral centers together with a remote diene function. The
preparation of this monocyclic species will utilize some aldol chemistry
which has been developed in our laboratories. Intramolecular [4 + 2]
cycloaddition of this monocyclic substance is expected to occur in the
exo-mode--closely following the stereochemical outcome of our own work on
the sesquiterpene, quadrone as well as the work of others. The
cycloaddition reaction yields a total of five chiral centers contained in a
tricyclic framework which represents rings B, C, and E of the target
natural product. Of particular importance is the securement of all three
sites of oxygenation in ring C in the correct stereochemical arrangement.
Further, the tircyclic substance contains both functionality and molecular
geometry suitable and conducive to the annulative elaboration of the rings
A and D present in this pentacyclic diterpene. A new reaction sequence
resulting in the formation of ring A will be used.
We also propose a total synthesis of the biologically very interesting
macrocyclic antibiotic, virginiamycin. We have divided this molecule into
two portions and named them the upper and lower halves. The upper fragment
utilizes some new and very useful erythro aldol methodology which features
the aldol-lactonization reaction of a vinylogous urethane. The methodology
should permit an extremely brief and efficient construction of the upper
half of virginiamycin. The lower fragment will be prepared from glutamic
acid and takes advantage of some sulfur based methodology we, and other,
developed some time ago. We have never used this methodology in a serious
synthetic setting and hope to do so during the course of our work on this
problem.
全合成具有高度细胞毒性的五环二萜,
项目成果
期刊论文数量(0)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
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RICHARD H SCHLESSINGER其他文献
RICHARD H SCHLESSINGER的其他文献
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{{ truncateString('RICHARD H SCHLESSINGER', 18)}}的其他基金
ENANTIOSELECTIVE (4+2) REACTIONS IN TOTAL SYNTHESIS
全合成中的对映选择性 (4 2) 反应
- 批准号:
2392184 - 财政年份:1996
- 资助金额:
$ 12.78万 - 项目类别:
ENANTIOSELECTIVE (4+2) REACTIONS IN TOTAL SYNTHESIS
全合成中的对映选择性 (4 2) 反应
- 批准号:
2187047 - 财政年份:1996
- 资助金额:
$ 12.78万 - 项目类别:
ASYMMETRIC DIELS-ALDER REACTIONS OF VINYLOGOUS URETHANES
乙烯基聚氨酯的不对称狄尔斯-阿尔德反应
- 批准号:
2187046 - 财政年份:1993
- 资助金额:
$ 12.78万 - 项目类别:
ASYMMETRIC DIELS-ALDER REACTIONS OF VINYLOGOUS URETHANES
乙烯基聚氨酯的不对称狄尔斯-阿尔德反应
- 批准号:
3308759 - 财政年份:1993
- 资助金额:
$ 12.78万 - 项目类别:
ASYMMETRIC DIELS-ALDER REACTIONS OF VINYLOGOUS URETHANES
乙烯基聚氨酯的不对称狄尔斯-阿尔德反应
- 批准号:
2187045 - 财政年份:1993
- 资助金额:
$ 12.78万 - 项目类别:
THE SYNTHESIS OF ROSARAMYCIN AND RELATED SYSTEMS
玫瑰霉素的合成及相关系统
- 批准号:
3128532 - 财政年份:1982
- 资助金额:
$ 12.78万 - 项目类别:
THE SYNTHESIS OF ROSARAMYCIN AND RELATED SYSTEMS
玫瑰霉素的合成及相关系统
- 批准号:
3128531 - 财政年份:1982
- 资助金额:
$ 12.78万 - 项目类别:
THE SYNTHESIS OF ROSARAMYCIN AND RELATED SYSTEMS
玫瑰霉素的合成及相关系统
- 批准号:
3128530 - 财政年份:1982
- 资助金额:
$ 12.78万 - 项目类别:
THE SYNTHESIS OF SOME COMPLEX CYTOTOXIC COMPOUNDS
一些复杂细胞毒性化合物的合成
- 批准号:
3168197 - 财政年份:1981
- 资助金额:
$ 12.78万 - 项目类别:
THE SYNTHESIS OF SOME COMPLEX CYTOTOXIC COMPOUNDS
一些复杂细胞毒性化合物的合成
- 批准号:
3168198 - 财政年份:1981
- 资助金额:
$ 12.78万 - 项目类别:
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