Abstract
Polyene macrolide antibiotics are naturally occurring antifungal agents. Members of this class include amphotericin B, which has been used widely to treat systemic fungal infections. A general synthetic strategy has been devised to prepare polyol chains associated with the polyene macrolides. Cyanohydrin acetonide alkylations were used to assemble the carbon skeleton, and a simple modification of the strategy allowed an advanced intermediate to be converted to either the candidin polyol or the nystatin polyol. The candidin polyol was further elaborated to a protected candidin aglycone. This strategy will be applicable to other members of the polyene macrolide natural products.
| Original language | English |
|---|---|
| Pages (from-to) | 11992-11995 |
| Number of pages | 4 |
| Journal | Proceedings of the National Academy of Sciences of the United States of America |
| Volume | 101 |
| Issue number | 33 |
| DOIs | |
| Publication status | Published - Aug 17 2004 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Genetics
- General
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A unified approach to polyene macrolides : Synthesis of candidin and nystatin polyols. / Kadota, Isao; Hu, Yueqing; Packard, Garrick K.; Rychnovsky, Scott D.
In: Proceedings of the National Academy of Sciences of the United States of America, Vol. 101, No. 33, 17.08.2004, p. 11992-11995.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A unified approach to polyene macrolides
T2 - Synthesis of candidin and nystatin polyols
AU - Kadota, Isao
AU - Hu, Yueqing
AU - Packard, Garrick K.
AU - Rychnovsky, Scott D.
PY - 2004/8/17
Y1 - 2004/8/17
N2 - Polyene macrolide antibiotics are naturally occurring antifungal agents. Members of this class include amphotericin B, which has been used widely to treat systemic fungal infections. A general synthetic strategy has been devised to prepare polyol chains associated with the polyene macrolides. Cyanohydrin acetonide alkylations were used to assemble the carbon skeleton, and a simple modification of the strategy allowed an advanced intermediate to be converted to either the candidin polyol or the nystatin polyol. The candidin polyol was further elaborated to a protected candidin aglycone. This strategy will be applicable to other members of the polyene macrolide natural products.
AB - Polyene macrolide antibiotics are naturally occurring antifungal agents. Members of this class include amphotericin B, which has been used widely to treat systemic fungal infections. A general synthetic strategy has been devised to prepare polyol chains associated with the polyene macrolides. Cyanohydrin acetonide alkylations were used to assemble the carbon skeleton, and a simple modification of the strategy allowed an advanced intermediate to be converted to either the candidin polyol or the nystatin polyol. The candidin polyol was further elaborated to a protected candidin aglycone. This strategy will be applicable to other members of the polyene macrolide natural products.
UR - http://www.scopus.com/inward/record.url?scp=4344666711&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=4344666711&partnerID=8YFLogxK
U2 - 10.1073/pnas.0401552101
DO - 10.1073/pnas.0401552101
M3 - Article
C2 - 15192147
AN - SCOPUS:4344666711
VL - 101
SP - 11992
EP - 11995
JO - Proceedings of the National Academy of Sciences of the United States of America
JF - Proceedings of the National Academy of Sciences of the United States of America
SN - 0027-8424
IS - 33
ER -