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Progress toward the total synthesis of securamine A :Construction of the securamine macrocyclic core

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Progress toward the total synthesis of securamine A :
其他題名:	Construction of the securamine macrocyclic core
作者:	Korakas, Peter.
面頁冊數:	300 p.
附註:	Director: John Louis Wood.
附註:	Source: Dissertation Abstracts International, Volume: 65-03, Section: B, page: 1328.
Contained By:	Dissertation Abstracts International65-03B.
標題:	Chemistry, Organic.
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3125233
ISBN:	0496725238

Progress toward the total synthesis of securamine A :Construction of the securamine macrocyclic core
Korakas, Peter.

Progress toward the total synthesis of securamine A :Construction of the securamine macrocyclic core [electronic resource] - 300 p.

Director: John Louis Wood.

Thesis (Ph.D.)--Yale University, 2004.

Applying knowledge gained from previous synthetic efforts has led to two corresponding synthetic approaches to the securamine A macrocyclic core. The first approach attempts to employ a copper mediated cross coupling between a primary amide and (Z)-vinyl iodide. The second strategy relies upon a well precedented lactone-to-lactam ring expansion (217--218 ).

ISBN: 0496725238Subjects--Topical Terms:

193634
Chemistry, Organic.

Progress toward the total synthesis of securamine A :Construction of the securamine macrocyclic core
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520 # $a Applying knowledge gained from previous synthetic efforts has led to two corresponding synthetic approaches to the securamine A macrocyclic core. The first approach attempts to employ a copper mediated cross coupling between a primary amide and (Z)-vinyl iodide. The second strategy relies upon a well precedented lactone-to-lactam ring expansion (217--218 ).
520 # $a In the latter sequence, an iodine monochloride reaction is employed to successfully functionalize the C2-C3 imidazole side chain. With the completed securamine macrocycle in hand, work stands only a few steps away from a completed natural product.
520 # $a Securamine A (1) is an unprecedented halogenated indole-imidazole alkaloid isolated from Securiflustra securifrons, a marine bryozoan native to the North Sea. It is one of seven natural product congeners, each composed of a pyrolloindole core along with a substituted imidazole connected by a modified isoprene unit on one end and a rare enamide moiety on the other. Herein are described efforts toward the total synthesis of this structurally unique alkaloid natural product.
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