The acid and base catalysed rearrangement products of pseudomonic acid A ( l a ) , derived from ( l a ) by intramolecular opening of the epoxide ring, have been shown to possess the trans-fused bicyclic structures (2a) and (3a). Structural assignments were made on the basis of the spectroscopic and chemical properties of (2a) and (3a) and their derivatives and confirmed by X-ray analysis. In strongly basic solution intramolecular rearrangement of (1 a) was accompanied by the loss of the nonanoate ester side chain and formation of (1 2a) and (1 3a).

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