Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)-γ-Rubromycin

Balancing act: The correct balance of electronic factors in the naphthazarin and isocoumarin fragments facilitates the acid‐mediated spiroketalization step to afford the key densely functionalized spiroketal (see picture; EOM=ethoxymethyl) in the formal synthesis of (±)‐γ‐rubromycin. A novel regiose...

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Published in:Angewandte Chemie (International ed.) 2009-10, Vol.48 (43), p.7996-8000
Main Authors: Rathwell, Dominea C.K, Yang, Sung-Hyun, Tsang, Kit Y, Brimble, Margaret A
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
antibiotics
azides
Benzene Derivatives - chemistry
Crystallography, X-Ray
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Humans
Isocoumarins - chemistry
Molecular Conformation
Naphthoquinones - chemistry
natural product synthesis
Quinones - chemical synthesis
Quinones - chemistry
spiroketals
Telomerase - antagonists & inhibitors
Telomerase - metabolism
total synthesis
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Summary:Balancing act: The correct balance of electronic factors in the naphthazarin and isocoumarin fragments facilitates the acid‐mediated spiroketalization step to afford the key densely functionalized spiroketal (see picture; EOM=ethoxymethyl) in the formal synthesis of (±)‐γ‐rubromycin. A novel regioselective allyloxylation/Claisen rearrangement of 2‐azido‐1,4‐naphthoquinone provides access to the highly oxygenated naphthazarin fragment.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200903316