Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins

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

Research output: Contribution to journalArticlepeer-review

101 Citations (Scopus)


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 languageEnglish
Pages (from-to)1699-1706
Number of pages8
JournalBulletin of the Chemical Society of Japan
Issue number6
Publication statusPublished - 1985
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)


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