A three-step entry to the aspirochlorine family of antifungal agents

Zhicai Wu; Lawrence J. Williams; Samuel J. Danishefsky

doi:10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E

A three-step entry to the aspirochlorine family of antifungal agents

Zhicai Wu, Lawrence J. Williams, Samuel J. Danishefsky

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

29 Scopus citations

Abstract

The quest for superior antifungal agents will be aided by the unprecedented sulfur migration of an epidithioketopiperazine (EDKP) in a highly stereoselective manner and in high yield. The rearrangement provides a short route to compounds in the same family as aspirochlorine (1), a potent inhibitor of fungal protein synthesis. In this family one of the dithio sulfur atoms is anchored to a dihydrobenzofuran ring that is spiro fused to the piperazine ring.

Original language	English (US)
Pages (from-to)	3866-3868
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	39
Issue number	21
DOIs	https://doi.org/10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E
State	Published - Nov 3 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

Keywords

Antifungal agents
Natural products
Rearrangements
Sulfur heterocycles

Access to Document

10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E

Cite this

@article{08cecd7645a74346a33c3da234e168e1,

title = "A three-step entry to the aspirochlorine family of antifungal agents",

abstract = "The quest for superior antifungal agents will be aided by the unprecedented sulfur migration of an epidithioketopiperazine (EDKP) in a highly stereoselective manner and in high yield. The rearrangement provides a short route to compounds in the same family as aspirochlorine (1), a potent inhibitor of fungal protein synthesis. In this family one of the dithio sulfur atoms is anchored to a dihydrobenzofuran ring that is spiro fused to the piperazine ring.",

keywords = "Antifungal agents, Natural products, Rearrangements, Sulfur heterocycles",

author = "Zhicai Wu and Williams, {Lawrence J.} and Danishefsky, {Samuel J.}",

year = "2000",

month = nov,

day = "3",

doi = "10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E",

language = "English (US)",

volume = "39",

pages = "3866--3868",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "21",

}

TY - JOUR

T1 - A three-step entry to the aspirochlorine family of antifungal agents

AU - Wu, Zhicai

AU - Williams, Lawrence J.

AU - Danishefsky, Samuel J.

PY - 2000/11/3

Y1 - 2000/11/3

N2 - The quest for superior antifungal agents will be aided by the unprecedented sulfur migration of an epidithioketopiperazine (EDKP) in a highly stereoselective manner and in high yield. The rearrangement provides a short route to compounds in the same family as aspirochlorine (1), a potent inhibitor of fungal protein synthesis. In this family one of the dithio sulfur atoms is anchored to a dihydrobenzofuran ring that is spiro fused to the piperazine ring.

AB - The quest for superior antifungal agents will be aided by the unprecedented sulfur migration of an epidithioketopiperazine (EDKP) in a highly stereoselective manner and in high yield. The rearrangement provides a short route to compounds in the same family as aspirochlorine (1), a potent inhibitor of fungal protein synthesis. In this family one of the dithio sulfur atoms is anchored to a dihydrobenzofuran ring that is spiro fused to the piperazine ring.

KW - Antifungal agents

KW - Natural products

KW - Rearrangements

KW - Sulfur heterocycles

UR - http://www.scopus.com/inward/record.url?scp=0034602034&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034602034&partnerID=8YFLogxK

U2 - 10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E

DO - 10.1002/1521-3773(20001103)39:21<3866::AID-ANIE3866>3.0.CO;2-E

M3 - Article

AN - SCOPUS:0034602034

SN - 1433-7851

VL - 39

SP - 3866

EP - 3868

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 21

ER -

A three-step entry to the aspirochlorine family of antifungal agents

Abstract

All Science Journal Classification (ASJC) codes

Keywords

Access to Document

Other files and links

Fingerprint

Cite this