Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction

Christian A. Kuttruff; Hendrik Zipse; Dirk Trauner

doi:10.1002/anie.201006154

Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction

Christian A. Kuttruff, Hendrik Zipse, Dirk Trauner

Chemistry

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

Abstract

A fusion of certain anthraquinones and diketopiperazines is an apt description of the variecolortides, a family of unusual fungal alkaloids. In a new, concise total synthesis of the variecolortides A and B, the natural racemates are obtained highly convergently and almost without protecting-group manipulations. The spirocyclic core is generated in a hetero-Diels-Alder reaction of a 1,4-anthraquinone with a didehydrodiketopiperazine.

Original language	English (US)
Pages (from-to)	1402-1405
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	6
DOIs	https://doi.org/10.1002/anie.201006154
State	Published - Feb 7 2011

Keywords

alkaloids
biomimetic synthesis
cascade reactions
cycloaddition
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

Access to Document

10.1002/anie.201006154

Cite this

@article{68b5e1850b6d48748990148a4605b8d3,

title = "Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction",

abstract = "A fusion of certain anthraquinones and diketopiperazines is an apt description of the variecolortides, a family of unusual fungal alkaloids. In a new, concise total synthesis of the variecolortides A and B, the natural racemates are obtained highly convergently and almost without protecting-group manipulations. The spirocyclic core is generated in a hetero-Diels-Alder reaction of a 1,4-anthraquinone with a didehydrodiketopiperazine.",

keywords = "alkaloids, biomimetic synthesis, cascade reactions, cycloaddition, total synthesis",

author = "Kuttruff, {Christian A.} and Hendrik Zipse and Dirk Trauner",

year = "2011",

month = feb,

day = "7",

doi = "10.1002/anie.201006154",

language = "English (US)",

volume = "50",

pages = "1402--1405",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "6",

}

TY - JOUR

T1 - Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction

AU - Kuttruff, Christian A.

AU - Zipse, Hendrik

AU - Trauner, Dirk

PY - 2011/2/7

Y1 - 2011/2/7

N2 - A fusion of certain anthraquinones and diketopiperazines is an apt description of the variecolortides, a family of unusual fungal alkaloids. In a new, concise total synthesis of the variecolortides A and B, the natural racemates are obtained highly convergently and almost without protecting-group manipulations. The spirocyclic core is generated in a hetero-Diels-Alder reaction of a 1,4-anthraquinone with a didehydrodiketopiperazine.

AB - A fusion of certain anthraquinones and diketopiperazines is an apt description of the variecolortides, a family of unusual fungal alkaloids. In a new, concise total synthesis of the variecolortides A and B, the natural racemates are obtained highly convergently and almost without protecting-group manipulations. The spirocyclic core is generated in a hetero-Diels-Alder reaction of a 1,4-anthraquinone with a didehydrodiketopiperazine.

KW - alkaloids

KW - biomimetic synthesis

KW - cascade reactions

KW - cycloaddition

KW - total synthesis

UR - http://www.scopus.com/inward/record.url?scp=79551658551&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79551658551&partnerID=8YFLogxK

U2 - 10.1002/anie.201006154

DO - 10.1002/anie.201006154

M3 - Article

C2 - 21290522

AN - SCOPUS:79551658551

SN - 1433-7851

VL - 50

SP - 1402

EP - 1405

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Concise total syntheses of variecolortides A and B through an unusual hetero-Diels-Alder reaction

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this