Concise Total Synthesis and Structure Assignment of TAN-1085

Rapid access to the tetracyclic core of TAN‐1085 (1) was possible by exploiting three efficient processes: a tandem electrocyclic reaction (A), a pinacol cyclization (B), and a regioselective monobenzoylation of a 1,2‐diol (C), which allowed the first total synthesis of 1.

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2004-06, Vol.43 (24), p.3167-3171
Main Authors: Ohmori, Ken, Mori, Keiji, Ishikawa, Yuji, Tsuruta, Hideyuki, Kuwahara, Shunsuke, Harada, Nobuyuki, Suzuki, Keisuke
Format: Article
Language:English
Subjects:
Alcohols - chemistry
Anti-Bacterial Agents - chemical synthesis
antibiotics
Circular Dichroism
Crystallography, X-Ray
Cyclization
Electrochemistry
electrocyclic reactions
glycosylation
Indicators and Reagents
Models, Molecular
Monosaccharides - chemical synthesis
Polycyclic Compounds - chemical synthesis
Stereoisomerism
Streptomyces - chemistry
structure elucidation
total synthesis
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Summary:Rapid access to the tetracyclic core of TAN‐1085 (1) was possible by exploiting three efficient processes: a tandem electrocyclic reaction (A), a pinacol cyclization (B), and a regioselective monobenzoylation of a 1,2‐diol (C), which allowed the first total synthesis of 1.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200453801