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Synthetic studies on the kalihinane ...
~
Keaney, Gregg F.
Synthetic studies on the kalihinane diterpenoids.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Synthetic studies on the kalihinane diterpenoids.
作者:
Keaney, Gregg F.
面頁冊數:
366 p.
附註:
Director: John Louis Wood.
附註:
Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5984.
Contained By:
Dissertation Abstracts International66-11B.
標題:
Chemistry, Organic.
電子資源:
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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Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5984.
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Thesis (Ph.D.)--Yale University, 2005.
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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.
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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.
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