Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues
Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide – dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquina...
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| Format: | Article |
| Language: | English |
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MDPI AG
2000-04-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/5/4/674/ |
| _version_ | 1811284579442491392 |
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| author | Veljko Dragojlovic |
| author_facet | Veljko Dragojlovic |
| author_sort | Veljko Dragojlovic |
| collection | DOAJ |
| description | Reaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide – dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane dienedione (9) by means of an 8-step sequence. |
| first_indexed | 2024-04-13T02:31:44Z |
| format | Article |
| id | doaj.art-f57361e52d02456ca285e4ea056f8e77 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-13T02:31:44Z |
| publishDate | 2000-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f57361e52d02456ca285e4ea056f8e772022-12-22T03:06:34ZengMDPI AGMolecules1420-30492000-04-015467469810.3390/50400674Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its AnaloguesVeljko DragojlovicReaction of enone (11) with the bifunctional Grignard reagent (7) in the presence of copper(I) bromide – dimethyl sulfide, followed by intramolecular alkylation of the resultant chloroketone (15) gave the tricyclic ketone (12). The tricyclic ketone (12) was transformed into the angular triquinane dienedione (9) by means of an 8-step sequence.http://www.mdpi.com/1420-3049/5/4/674/Subergorgic acidsesquiterpenoid synthesismethylenecyclopentane annulationbifunctional reagentstriquinane synthesis |
| spellingShingle | Veljko Dragojlovic Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues Molecules Subergorgic acid sesquiterpenoid synthesis methylenecyclopentane annulation bifunctional reagents triquinane synthesis |
| title | Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues |
| title_full | Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues |
| title_fullStr | Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues |
| title_full_unstemmed | Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues |
| title_short | Synthesis of a Highly Functionalized Triquinane: Studies Towards a Total Synthesis of Subergorgic Acid and Its Analogues |
| title_sort | synthesis of a highly functionalized triquinane studies towards a total synthesis of subergorgic acid and its analogues |
| topic | Subergorgic acid sesquiterpenoid synthesis methylenecyclopentane annulation bifunctional reagents triquinane synthesis |
| url | http://www.mdpi.com/1420-3049/5/4/674/ |
| work_keys_str_mv | AT veljkodragojlovic synthesisofahighlyfunctionalizedtriquinanestudiestowardsatotalsynthesisofsubergorgicacidanditsanalogues |