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Stereoretentive Nuc...
Stereoretentive Nucleophilic Substitution at the Tetrasubstituted Carbon of Galiellalactone
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- Escobar, Zilma (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Nilsson, Jakob (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Gidlöf, Ritha (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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- Johansson, Martin (author)
- Glactone Pharma Development AB
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- Sterner, Olov (author)
- Lund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH
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(creator_code:org_t)
- 2020-05-18
- 2020
- English 7 s.
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In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 85:12, s. 7704-7710
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http://dx.doi.org/10...
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Abstract
Subject headings
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- The fungal metabolite galiellalactone (1) was, as its acetate 4, discovered to undergo a substitution reaction with cysteine derivatives. By studying the reaction mechanism and the intermediates formed, and in an effort to expand the chemical diversity of the galiellalactonoids, a mild and general method of preparing ether, thioether, and amine analogues of galiellalactone was developed. The reaction is a formal stereoretentive nucleophilic substitution at an oxygenated tertiary carbon. NMR analysis of the progressing reaction shows that it involves an initial allylic substitution to form a new Michael acceptor, followed by the addition of a second equivalent of the nucleophile to this and, finally, a retro Michael reaction. This restores the original galiellalactone system with a double bond between C-2a and C-3, but with a new substituent at C-7b. As galiellalactone is a promising STAT3 inhibitor, this novel transformation facilitates the semisynthesis of a wide variety of new analogues for structure-activity relationship studies.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Publication and Content Type
- art (subject category)
- ref (subject category)
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