Rapid Access to the Tricyclic Spirotetronic Core of Abyssomicins

Abyssomicins, a novel class of polyketide antibiotics, are characterized by an unprecedented spirotetronic tricyclic subunit in their structure. In this letter, a short synthesis of a suitably functionalized tricyclic precursor of abyssomicins is reported. Key steps of the synthesis are (i) the high...

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Bibliographic Details
Published in:Organic letters 2005-09, Vol.7 (20), p.4515-4518
Main Authors: Zografos, Alexandros L, Yiotakis, Athanasios, Georgiadis, Dimitris
Format: Article
Language:English
Subjects:
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Cyclization
Epoxy Compounds - chemistry
Lactones - chemistry
Molecular Structure
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Time Factors
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Summary:Abyssomicins, a novel class of polyketide antibiotics, are characterized by an unprecedented spirotetronic tricyclic subunit in their structure. In this letter, a short synthesis of a suitably functionalized tricyclic precursor of abyssomicins is reported. Key steps of the synthesis are (i) the highly stereoselective Al(III)-tethered Diels−Alder reaction and (ii) the tandem Dieckmann cyclization/TBS trapping of the C9 hydroxyl group followed by a regioselective intramolecular epoxide opening for the assembly of the target tricyclic structure.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol051872e