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Synthetic studies on the kalihinane ...

Keaney, Gregg F.

Synthetic studies on the kalihinane diterpenoids.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Synthetic studies on the kalihinane diterpenoids.
Author:	Keaney, Gregg F.
Description:	366 p.
Notes:	Director: John Louis Wood.
Notes:	Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5984.
Contained By:	Dissertation Abstracts International66-11B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3194669
ISBN:	9780542394348

Synthetic studies on the kalihinane diterpenoids.
Keaney, Gregg F.

Synthetic studies on the kalihinane diterpenoids. - 366 p.

Director: John Louis Wood.

Thesis (Ph.D.)--Yale University, 2005.

In light of the fascinating chemical structures and intriguing biological profile of members of the kalihinane family, a project directed towards the total synthesis of 1 and related kalihinanes has been conducted. In 2003, the first total synthesis of (+/-)-kalihinol C ((+/-)- 3) was accomplished, the synthetic strategy of which relied upon a series of substrate-controlled, diastereoselective reactions in order to functionalize the decalin core (66→67, 68→69, 77→82) and install the pendant tetrahydrofuran ring (82G→83, 82→84, 88→89 ). Current efforts in our laboratory have been focused upon the total synthesis of 1 with an emphasis upon improving the efficiency of the aziridination reaction (77→150a, 77→174) and the development of novel synthetic methodology. Such efforts have led to the application of rhodium (II) perfluorobutyramide (199) in conducting a variety of olefin aziridinations (200→202-4). Furthermore, a series of kalihinane analogs have been synthesized and assayed in an effort to understand the role of the kalihinane carbocycle and the isonitriles in antimalarial activity.

ISBN: 9780542394348Subjects--Topical Terms:

193634
Chemistry, Organic.

Synthetic studies on the kalihinane diterpenoids.
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100 0 $a Keaney, Gregg F. $3 244972
245 1 0 $a Synthetic studies on the kalihinane diterpenoids.
300 $a 366 p.
500 $a Director: John Louis Wood.
500 $a Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5984.
502 $a Thesis (Ph.D.)--Yale University, 2005.
520 # $a In light of the fascinating chemical structures and intriguing biological profile of members of the kalihinane family, a project directed towards the total synthesis of 1 and related kalihinanes has been conducted. In 2003, the first total synthesis of (+/-)-kalihinol C ((+/-)- 3) was accomplished, the synthetic strategy of which relied upon a series of substrate-controlled, diastereoselective reactions in order to functionalize the decalin core (66→67, 68→69, 77→82) and install the pendant tetrahydrofuran ring (82G→83, 82→84, 88→89 ). Current efforts in our laboratory have been focused upon the total synthesis of 1 with an emphasis upon improving the efficiency of the aziridination reaction (77→150a, 77→174) and the development of novel synthetic methodology. Such efforts have led to the application of rhodium (II) perfluorobutyramide (199) in conducting a variety of olefin aziridinations (200→202-4). Furthermore, a series of kalihinane analogs have been synthesized and assayed in an effort to understand the role of the kalihinane carbocycle and the isonitriles in antimalarial activity.
520 # $a Kalihinol A (1) was isolated from the Guamanian marine sponge Acanthella cavernosa in 1984. To date, more than forty compounds (2-46) related to 1 have been isolated, and many of these highly-functionalized diterpenoids possess very unique biological activities. In particular, 1 has been shown to exhibit extremely potent antimalarial activity against Plasmodium falciparum.
590 $a School code: 0265.
650 # 0 $a Chemistry, Organic. $3 193634
650 # 0 $a Chemistry, Pharmaceutical. $3 206042
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710 0 # $a Yale University. $3 212430
773 0 # $g 66-11B. $t Dissertation Abstracts International
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790 1 0 $a Wood, John Louis, $e advisor
791 $a Ph.D.
792 $a 2005
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