語系:
繁體中文
English
說明(常見問題)
圖資館首頁
登入
回首頁
切換:
標籤
|
MARC模式
|
ISBD
Studies toward the total synthesis o...
~
University of Pennsylvania.
Studies toward the total synthesis of purpuromycin. Synthesis of bisbenzannelated 5,6-spiroketals via a [3+2] dipolar cycloaddition strategy.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Studies toward the total synthesis of purpuromycin. Synthesis of bisbenzannelated 5,6-spiroketals via a [3+2] dipolar cycloaddition strategy.
作者:
Waters, Stephen Paul.
面頁冊數:
419 p.
附註:
Source: Dissertation Abstracts International, Volume: 65-06, Section: B, page: 2943.
附註:
Supervisor: Marisa C. Kozlowski.
Contained By:
Dissertation Abstracts International65-06B.
標題:
Chemistry, Organic.
電子資源:
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3138089
ISBN:
0496852590
Studies toward the total synthesis of purpuromycin. Synthesis of bisbenzannelated 5,6-spiroketals via a [3+2] dipolar cycloaddition strategy.
Waters, Stephen Paul.
Studies toward the total synthesis of purpuromycin. Synthesis of bisbenzannelated 5,6-spiroketals via a [3+2] dipolar cycloaddition strategy.
- 419 p.
Source: Dissertation Abstracts International, Volume: 65-06, Section: B, page: 2943.
Thesis (Ph.D.)--University of Pennsylvania, 2004.
*Please refer to dissertation for diagrams.
ISBN: 0496852590Subjects--Topical Terms:
193634
Chemistry, Organic.
Studies toward the total synthesis of purpuromycin. Synthesis of bisbenzannelated 5,6-spiroketals via a [3+2] dipolar cycloaddition strategy.
LDR
:03262nmm _2200301 _450
001
162798
005
20051017073524.5
008
090528s2004 eng d
020
$a
0496852590
035
$a
00149299
040
$a
UnM
$c
UnM
100
0
$a
Waters, Stephen Paul.
$3
227942
245
1 0
$a
Studies toward the total synthesis of purpuromycin. Synthesis of bisbenzannelated 5,6-spiroketals via a [3+2] dipolar cycloaddition strategy.
300
$a
419 p.
500
$a
Source: Dissertation Abstracts International, Volume: 65-06, Section: B, page: 2943.
500
$a
Supervisor: Marisa C. Kozlowski.
502
$a
Thesis (Ph.D.)--University of Pennsylvania, 2004.
520
#
$a
*Please refer to dissertation for diagrams.
520
#
$a
A new method for the construction of bisbenzannelated spiroketals was developed consisting of [3+2] cycloaddition of nitrile oxides with olefins, reduction of the resulting isoxazoline to beta-keto alcohols (formal aldol products), and subsequent spirocyclization. This method was successfully utilized for the construction of the 5,6-spiroketal core of purpuromycin. Spectroscopic and crystallographic analysis of each diastereomeric spiroketal product, in conjunction with spectroscopic data obtained from a sample of natural purpuromycin, led to an assignment of the hitherto unknown relative configuration of the natural product.*
520
#
$a
Efficient syntheses of the isocoumarin and naphthalene fragments were established. Key features of the isocoumarin synthesis include the desymmetrization of a functionalized catechol and a Heck coupling/lactonization sequence. Two routes for the naphthalene fragment were established: one based on a Dotz chromium carbene cyclization and the other following a more traditional Diels-Alder approach.
520
#
$a
Fragment coupling of the fully functionalized isocoumarin and naphthalene fragments of purpuromycin was achieved by the [3+2] cycloaddition protocol. Although subsequent spirocyclization of an advanced intermediate was not realized, the factors responsible for inefficient spiroketal formation were identified through the sequential coupling of each fragment with a suitable model counterpart. While the naphthalene fragment is a willing participant in spirocyclization, the isocoumarin fragment, due to inductive effects from the electron-deficient lactone moiety, is not sufficiently nucleophilic for attack and ring closure. From these findings, a modified synthesis is currently underway in which the isocoumarin fragment is installed in a reduced form prior to spirocyclization.*
520
#
$a
This dissertation describes studies toward the total synthesis of purpuromycin. Consisting of naphthazarin and isocoumarin ring systems linked through a unique bisbenzannelated 5,6-spiroketal core, purpuromycin shows cytotoxic activity against Gram-positive bacteria, fungi, protozoa, and a number of tumor cell lines.*
590
$a
School code: 0175.
650
# 0
$a
Chemistry, Organic.
$3
193634
690
$a
0490
710
0 #
$a
University of Pennsylvania.
$3
212781
773
0 #
$g
65-06B.
$t
Dissertation Abstracts International
790
$a
0175
790
1 0
$a
Kozlowski, Marisa C.,
$e
advisor
791
$a
Ph.D.
792
$a
2004
856
4 0
$u
http://libsw.nuk.edu.tw:81/login?url=http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3138089
$z
http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3138089
筆 0 讀者評論
全部
電子館藏
館藏
1 筆 • 頁數 1 •
1
條碼號
館藏地
館藏流通類別
資料類型
索書號
使用類型
借閱狀態
預約狀態
備註欄
附件
000000001291
電子館藏
1圖書
學位論文
一般使用(Normal)
在架
0
1 筆 • 頁數 1 •
1
多媒體
多媒體檔案
http://libsw.nuk.edu.tw:81/login?url=http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3138089
評論
新增評論
分享你的心得
Export
取書館別
處理中
...
變更密碼
登入