Synthesis of reported and revised structures of amathamide D and synthesis of convolutamine F, H and lutamide A, C

Khan, Faiz Ahmed and Ahmad, S (2012) Synthesis of reported and revised structures of amathamide D and synthesis of convolutamine F, H and lutamide A, C. Journal of Organic Chemistry, 77 (5). pp. 2389-2397. ISSN 0022-3263

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Abstract

Total synthesis of the published structure of amathamide D is described. Methyl 2,3,4-tribromo-5-hydroxybenzoate was selected as starting compound because it is readily accessible via acid-mediated Grob fragmentation- aromatization reaction of 1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5- en-2-one. The aforementioned ester was transformed into the reported structure of amathamide D through methylation of a hydroxyl group and conversion of the ester moiety to a β-aminoethyl side chain. The NMR data of the synthetic compound did not conform to the reported natural product structure possessing contiguously positioned β-aminoethyl side chain, a set of three adjacent bromines, and a methyl ether linkage on the phenyl ring. This prompted us to redefine the natural product structure by synthesizing a product whose spectral data exactly matched with the reported data of amathamide D. The convolutamine H, with completely substituted phenyl ring adorned with an extra methyl ether functional group, has also been synthesized by application of Grob fragmentation-aromatization strategy to 3-(benzyloxy)-1,4,5,6-tetrabromo-7,7- dimethoxybicyclo[2.2.1]hept-5-en-2-one. This approach furnished directly methyl 2,3,4-tribromo-5,6-dimethoxybenzoate, which was converted straightforwardly into convolutamine H. Further, synthesis of convolutamine F and lutamide A and C is also described. © 2012 American Chemical Society.

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IITH Creators:
IITH CreatorsORCiD
Khan, Faiz AhmedUNSPECIFIED
Item Type: Article
Uncontrolled Keywords: Aromatization reactions; Ester moieties; Grob fragmentation; Hydroxyl groups; Methyl ethers; Natural products; NMR data; Phenyl rings; Side-chains; Spectral data; Starting compounds; Synthetic compounds; Total synthesis
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: Mr. Siva Shankar K
Date Deposited: 14 Oct 2014 10:45
Last Modified: 21 Sep 2017 06:45
URI: http://raiith.iith.ac.in/id/eprint/455
Publisher URL: https://doi.org/10.1021/jo3000173
OA policy: http://www.sherpa.ac.uk/romeo/issn/0022-3263/
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