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 | |
| Publication status | Published - Jan 1 1985 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
Cite this
Enantiodivergent total syntheses of nanaomycins and their enantiomers, kalafungins. / Tatsuta, Kuniaki; Akimoto, Kohji; Annaka, Masahiko; Ohno, Yutaka; Kinoshita, Mitsuhiro.
In: Bulletin of the Chemical Society of Japan, Vol. 58, No. 6, 01.01.1985, p. 1699-1706.Research output: Contribution to journal › Article
}
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
PY - 1985/1/1
Y1 - 1985/1/1
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.
UR - http://www.scopus.com/inward/record.url?scp=0021927869&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0021927869&partnerID=8YFLogxK
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 -