A unified approach to polyene macrolides: Synthesis of candidin and nystatin polyols

Isao Kadota; Yueqing Hu; Garrick K. Packard; Scott D. Rychnovsky

doi:10.1073/pnas.0401552101

A unified approach to polyene macrolides: Synthesis of candidin and nystatin polyols

Isao Kadota, Yueqing Hu, Garrick K. Packard, Scott D. Rychnovsky

Research output: Contribution to journal › Article

20 Citations (Scopus)

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	https://doi.org/10.1073/pnas.0401552101
Publication status	Published - Aug 17 2004
Externally published	Yes

ASJC Scopus subject areas

General

Access to Document

10.1073/pnas.0401552101

Fingerprint Dive into the research topics of 'A unified approach to polyene macrolides: Synthesis of candidin and nystatin polyols'. Together they form a unique fingerprint.

Cite this

Kadota, I., Hu, Y., Packard, G. K., & Rychnovsky, S. D. (2004). A unified approach to polyene macrolides: Synthesis of candidin and nystatin polyols. Proceedings of the National Academy of Sciences of the United States of America, 101(33), 11992-11995. https://doi.org/10.1073/pnas.0401552101

@article{edf48c4c8cf54e028d984ab3a86ad189,

title = "A unified approach to polyene macrolides: Synthesis of candidin and nystatin polyols",

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.",

author = "Isao Kadota and Yueqing Hu and Packard, {Garrick K.} and Rychnovsky, {Scott D.}",

year = "2004",

month = aug,

day = "17",

doi = "10.1073/pnas.0401552101",

language = "English",

volume = "101",

pages = "11992--11995",

journal = "Proceedings of the National Academy of Sciences of the United States of America",

issn = "0027-8424",

publisher = "National Academy of Sciences",

number = "33",

}

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 -