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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Bibliographic Details
Published in:Organic letters 2001-12, Vol.3 (25), p.4015-4018
Main Authors: Akai, Shuji, Tsujino, Toshiaki, Fukuda, Nobuhisa, Iio, Kiyosei, Takeda, Yoshifumi, Kawaguchi, Ken-ichi, Naka, Tadaatsu, Higuchi, Kazuhiro, Kita, Yasuyuki
Format: Article
Language:English
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
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016696y