Enantiodivergent Synthesis of Either Enantiomer of ABCDE-Ring Analogue of Antitumor Antibiotic Fredericamycin A via Intramolecular [4 + 2] Cycloaddition Approach
An intramolecular enantiodivergent synthesis of both enantiomers of the ABCDE-ring analogue 22 of fredericamycin A is reported. Key steps involve an intramolecular [4 + 2] cycloaddition of 17 and an aromatic Pummerer-type reaction of 19. A lipase-catalyzed enantioselective desymmetrization of prochi...
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| Veröffentlicht in: | Organic letters 2001-12, Vol.3 (25), p.4015-4018 |
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| container_issue | 25 |
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| container_title | Organic letters |
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| creator | Akai, Shuji Tsujino, Toshiaki Fukuda, Nobuhisa Iio, Kiyosei Takeda, Yoshifumi Kawaguchi, Ken-ichi Naka, Tadaatsu Higuchi, Kazuhiro Kita, Yasuyuki |
| description | An intramolecular enantiodivergent synthesis of both enantiomers of the ABCDE-ring analogue 22 of fredericamycin A is reported. Key steps involve an intramolecular [4 + 2] cycloaddition of 17 and an aromatic Pummerer-type reaction of 19. A lipase-catalyzed enantioselective desymmetrization of prochiral diol 2 using 1-ethoxyvinyl 2-furoate 3 led to the pivotal intermediate (R)-4. |
| doi_str_mv | 10.1021/ol016696y |
| format | Article |
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Lett</addtitle><date>2001-12-13</date><risdate>2001</risdate><volume>3</volume><issue>25</issue><spage>4015</spage><epage>4018</epage><pages>4015-4018</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An intramolecular enantiodivergent synthesis of both enantiomers of the ABCDE-ring analogue 22 of fredericamycin A is reported. Key steps involve an intramolecular [4 + 2] cycloaddition of 17 and an aromatic Pummerer-type reaction of 19. A lipase-catalyzed enantioselective desymmetrization of prochiral diol 2 using 1-ethoxyvinyl 2-furoate 3 led to the pivotal intermediate (R)-4.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>11735573</pmid><doi>10.1021/ol016696y</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2001-12, Vol.3 (25), p.4015-4018 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Antibiotics, Antineoplastic - chemical synthesis Antibiotics, Antineoplastic - chemistry Candida - enzymology Circular Dichroism Humans Isoquinolines - chemical synthesis Isoquinolines - chemistry Lipase - metabolism Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Spiro Compounds - chemical synthesis Spiro Compounds - chemistry Stereoisomerism |
| title | Enantiodivergent Synthesis of Either Enantiomer of ABCDE-Ring Analogue of Antitumor Antibiotic Fredericamycin A via Intramolecular [4 + 2] Cycloaddition Approach |
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