Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins

Kuniaki Tatsuta; Kohji Akimoto; Masahiko Annaka; Yutaka Ohno; Mitsuhiro Kinoshita

doi:10.1246/bcsj.58.1699

Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins

Kuniaki Tatsuta, Kohji Akimoto, Masahiko Annaka, Yutaka Ohno, Mitsuhiro Kinoshita

Research output: Contribution to journal › Article

94 Citations (Scopus)

Abstract

The first, enantiospecific total syntheses of pyranonaphthoquinone antibiotics, nanaomycins D and A, and their enantiomers, kalafungin and 4-deoxykalafunginic acid are described by an "enantiodivergent" strategy from a common optically active intermediate, (lS,3RS,4S)-3,4-dihydro-5,9,10-trimethoxy-l-methyl-lH-naphtho[2,3-c]pyran-3,4-diol, which has been derived from L-rhamnose via condensation of 4-methoxy-3-(phenylsulfonyl)-l(3//)-isobenzofuranone and methyl 3,4,6-trideoxy-a-L-g/ylero-hex-3-enopyranosid-2-ulose.

Original language	English
Pages (from-to)	1699-1706
Number of pages	8
Journal	Bulletin of the Chemical Society of Japan
Volume	58
Issue number	6
DOIs	https://doi.org/10.1246/bcsj.58.1699
Publication status	Published - Jan 1 1985
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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Tatsuta, K., Akimoto, K., Annaka, M., Ohno, Y., & Kinoshita, M. (1985). Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins. Bulletin of the Chemical Society of Japan, 58(6), 1699-1706. https://doi.org/10.1246/bcsj.58.1699

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