Total Synthesis of Macbecin I

Beyond the bounds of biosynthesis: In a step towards the goal of developing a synthetic pathway for the production of collections of complex molecules related to the benzoquinone ansamycin antibiotics, a natural member of this class was synthesized in a convergent manner through the mild titanium al...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-05, Vol.47 (21), p.4005-4008
Main Authors: Belardi, Justin K, Micalizio, Glenn C
Format: Article
Language:English
Subjects:
ansamycin antibiotics
Benzoquinones - chemical synthesis
Benzoquinones - chemistry
cross-coupling
Lactams, Macrocyclic - chemical synthesis
Lactams, Macrocyclic - chemistry
Molecular Conformation
natural products
Stereoisomerism
titanium
total synthesis
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Summary:Beyond the bounds of biosynthesis: In a step towards the goal of developing a synthetic pathway for the production of collections of complex molecules related to the benzoquinone ansamycin antibiotics, a natural member of this class was synthesized in a convergent manner through the mild titanium alkoxide mediated coupling of the highly functionalized aniline‐containing alkyne 1 with the sensitive polyunsaturated aldehyde 2.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200800400