DSpace
 

DSpace at IIT Bombay >
IITB Publications >
Review >

Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/3115

Title: Angucyclinone antibiotics: total syntheses of ym-181741, (+)-ochromycinone, (+)-rubiginone b-2, (-)-tetrangomycin, and mm-47755
Authors: KALIAPPAN, KP
RAVIKUMAR, V
Issue Date: 2007
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY,72(16)6116-6126
Abstract: A concise and highly enantioselective route has been developed for the synthesis of angucyclinone-type natural products. Utilizing this strategy, total syntheses of five natural products YM-181741, (+)-ochromycinone, (+)-rubiginone B-2, (-)-tetrangomycin, and MM-47755 have been accomplished in 22%, 23%, 19%, 18%, and 12% overall yields, respectively. Our approach for the synthesis of these natural products having the benz[a]anthraquinone skeleton is based on a sequential intramolecular enyne metathesis, intermolecular Diels-Alder reaction (DAR), and aromatization. The intramolecular enyne metathesis reaction was employed for the synthesis of enantiopure 1,3-dienes in excellent yields. Furthermore, the synthesis of YM-181741 as well as structurally similar angucyclinones such as (+)-ochromycinone and (+)-rubiginone B-2 was achieved via asymmetric enolate alkylation of an oxazolidinone in excellent de. The related angucyclinones (-)-tetrangomycin and MM-47755, bearing a labile tertiary alcohol, were synthesized via Sharpless asymmetric epoxidation of a known allylic alcohol followed by opening the epoxide with Red-Al. The introduction of oxygen functionality at C-1 in all these natural products was accomplished by photooxygenation under a positive pressure of oxygen.
URI: http://dx.doi.org/10.1021/jo070709p
http://dspace.library.iitb.ac.in/xmlui/handle/10054/13936
http://hdl.handle.net/100/3115
ISSN: 0022-3263
Appears in Collections:Review

Files in This Item:

There are no files associated with this item.

View Statistics

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

 

Valid XHTML 1.0! DSpace Software Copyright © 2002-2010  Duraspace - Feedback