Synthesis of 35-deoxy amphotericin B methyl ester: A strategy for molecular editing

Alex M. Szpilman; Damiano M. Cereghetti; Nicholas R. Wurtz; Jeffrey M. Manthorpe; Erick M. Carreira

doi:10.1002/anie.200800589

Synthesis of 35-deoxy amphotericin B methyl ester: A strategy for molecular editing

Alex M. Szpilman, Damiano M. Cereghetti, Nicholas R. Wurtz, Jeffrey M. Manthorpe, Erick M. Carreira

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

(Chemical Presented) A modular strategy for the assembly of amphotericin B analogues with modifications in the macrolactone ring relies on the efficient gram-scale synthesis of all major and minor motifs of amphotericin B. Proof of concept has been achieved by the preparation of the 35-deoxy aglycone en route to the long-sought-after 35-deoxy analogue of amphotericin B.

Original language	English
Pages (from-to)	4335-4338
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	23
DOIs	https://doi.org/10.1002/anie.200800589
State	Published - 26 May 2008
Externally published	Yes

Keywords

Amphotericin B
Antifungal agents
Asymmetric synthesis
Natural products
Total synthesis

Access to Document

10.1002/anie.200800589

Cite this

@article{1eb3480a4d344e42926a2fc5546fd35d,

title = "Synthesis of 35-deoxy amphotericin B methyl ester: A strategy for molecular editing",

abstract = "(Chemical Presented) A modular strategy for the assembly of amphotericin B analogues with modifications in the macrolactone ring relies on the efficient gram-scale synthesis of all major and minor motifs of amphotericin B. Proof of concept has been achieved by the preparation of the 35-deoxy aglycone en route to the long-sought-after 35-deoxy analogue of amphotericin B.",

keywords = "Amphotericin B, Antifungal agents, Asymmetric synthesis, Natural products, Total synthesis",

author = "Szpilman, \{Alex M.\} and Cereghetti, \{Damiano M.\} and Wurtz, \{Nicholas R.\} and Manthorpe, \{Jeffrey M.\} and Carreira, \{Erick M.\}",

year = "2008",

month = may,

day = "26",

doi = "10.1002/anie.200800589",

language = "אנגלית",

volume = "47",

pages = "4335--4338",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "23",

}

TY - JOUR

T1 - Synthesis of 35-deoxy amphotericin B methyl ester

T2 - A strategy for molecular editing

AU - Szpilman, Alex M.

AU - Cereghetti, Damiano M.

AU - Wurtz, Nicholas R.

AU - Manthorpe, Jeffrey M.

AU - Carreira, Erick M.

PY - 2008/5/26

Y1 - 2008/5/26

N2 - (Chemical Presented) A modular strategy for the assembly of amphotericin B analogues with modifications in the macrolactone ring relies on the efficient gram-scale synthesis of all major and minor motifs of amphotericin B. Proof of concept has been achieved by the preparation of the 35-deoxy aglycone en route to the long-sought-after 35-deoxy analogue of amphotericin B.

AB - (Chemical Presented) A modular strategy for the assembly of amphotericin B analogues with modifications in the macrolactone ring relies on the efficient gram-scale synthesis of all major and minor motifs of amphotericin B. Proof of concept has been achieved by the preparation of the 35-deoxy aglycone en route to the long-sought-after 35-deoxy analogue of amphotericin B.

KW - Amphotericin B

KW - Antifungal agents

KW - Asymmetric synthesis

KW - Natural products

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/46749120632

U2 - 10.1002/anie.200800589

DO - 10.1002/anie.200800589

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

C2 - 18454441

AN - SCOPUS:46749120632

SN - 1433-7851

VL - 47

SP - 4335

EP - 4338

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 23

ER -

Synthesis of 35-deoxy amphotericin B methyl ester: A strategy for molecular editing

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this