Studies Directed toward the Total Synthesis of Lactonamycin: Control of the Sense of Cycloaddition of a Quinone through Directed Intramolecular Catalysis | Health & Environmental Research Online (HERO)

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Citation
Tags

HERO ID

8159193

Reference Type

Journal Article

Title

Studies Directed toward the Total Synthesis of Lactonamycin: Control of the Sense of Cycloaddition of a Quinone through Directed Intramolecular Catalysis

Author(s)

Cox, CD; Siu, T; Danishefsky, SJ

Year

2003

Is Peer Reviewed?

Yes

Journal

Angewandte Chemie (International Edition)
ISSN: 1433-7851
EISSN: 1521-3773

Volume

Issue

Page Numbers

5625-5629

Language

English

DOI

10.1002/anie.200352591

Abstract

The rapid assembly of the ABCD tetracyclic ring system of lactonamycin involved the strong-base-induced regioselective Diels-Alder reaction of 1 and 2 to form advanced precursor 3. Regiochemical control results from the suitably positioned hydroxy group, and thus only the desired isomer of 3 is obtained.

Keywords

Antibiotics; Diels-Alder reaction; Natural products; Quinones; Total synthesis