TY - JOUR
T1 - Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins
AU - Tatsuta, Kuniaki
AU - Akimoto, Kohji
AU - Annaka, Masahiko
AU - Ohno, Yutaka
AU - Kinoshita, Mitsuhiro
N1 - Publisher Copyright:
© 1985 The Chemical Society of Japan.
Copyright:
Copyright 2018 Elsevier B.V., All rights reserved.
PY - 1985
Y1 - 1985
N2 - 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.
AB - 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.
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U2 - 10.1246/bcsj.58.1699
DO - 10.1246/bcsj.58.1699
M3 - Article
AN - SCOPUS:0021927869
VL - 58
SP - 1699
EP - 1706
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 6
ER -