Enantiodivergent synthesis of either enantiomer of ABCDE-ring analogue of antitumor antibiotic fredericamycin A via intramolecular [4 + 2] cycloaddition approach

S Akai; T Tsujino; N Fukuda; K Iio; Y Takeda; K Kawaguchi Ki; T Naka; K Higuchi; Y Kita

doi:10.1021/ol016696y

Enantiodivergent synthesis of either enantiomer of ABCDE-ring analogue of antitumor antibiotic fredericamycin A via intramolecular [4 + 2] cycloaddition approach

Org Lett. 2001 Dec 13;3(25):4015-8. doi: 10.1021/ol016696y.

Authors

S Akai¹, T Tsujino, N Fukuda, K Iio, Y Takeda, K Kawaguchi Ki, T Naka, K Higuchi, Y Kita

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 11735573
DOI: 10.1021/ol016696y

Abstract

[reaction: see text] 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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

Antibiotics, Antineoplastic
Isoquinolines
Spiro Compounds
Lipase
fredericamycin A