Second‐generation total synthesis of the pigment Aurantricholone
Abstract: Our first total synthesis of aurantricholone established its benzotropolone core by the ring-enlargement of a tetralone. Here we describe another total synthesis of aurantricholone. It reaches the benzotropolone core from a known olefin metathesis product via an equally known dibromide, both of which contain a ketoketal moiety. The next transformation - step 9 overall - engaged this motif in a β-elimination of ROH rather than in a hydrolysis under the forcing acidic conditions indispensable in all prior benzotropolone preparations from such an intermediate. In step 10, the Csp2−Br bonds of the elimination product underwent two doubly Z-selective Suzuki couplings with a boronylated O-methyl 4-methylidenetetronate. This gave penta(O-methyl)aurantricholone. Its NMR shifts matched essentially those of a derivative of natural aurantricholone by Steglich et al. Three O−Me bonds were cleaved with BBr3/CH2Cl2 (step 11) and two O−Me bonds with LiBr/DMF (step 12). A 1 : 3 co-crystal of aurantricholone and DMSO allowed for an X-ray structure analysis
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Notes
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European journal of organic chemistry. - 26, 42 (2023) , e202300648, ISSN: 1099-0690
- Event
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Veröffentlichung
- (where)
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Freiburg
- (who)
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Universität
- (when)
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2023
- Creator
- DOI
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10.1002/ejoc.202300648
- URN
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urn:nbn:de:bsz:25-freidok-2402991
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
14.08.2025, 10:45 AM CEST
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Koblischek, Philip
- Brückner, Reinhard
- Universität
Time of origin
- 2023
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