Abstract
The B-rings (2,5- trans-tetrahydrofurans) of lasalocid A ( 6) and isolasalocid A ( 7) were stereoselectively constructed from the corresponding p-methoxyphenylallyl alcohols ( 13a, 13b) by treatment with ZnBr 2 to give C 13-C 24 fragments ( 14a, 14b) via a new chelation-controlled cyclization under thermodynamic conditions. After their conversion into lasalocid ketone ( 19) and BOM-isolasalocid ketone ( 20), coupling with the C 1-C 11 aldehyde ( 22) completed the synthesis of 6 and 7, respectively.
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