Rapid access to the tricyclic spirotetronic core of abyssomicins.
[reaction: see text] 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.
Zografos
Alexandros L
AL
Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece.
Yiotakis
Athanasios
A
Georgiadis
Dimitris
D
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013997:Time Factors
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds; D007783:Lactones; D011083:Polycyclic Compounds