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The title compound 1 has been prepared, for the first time, in six steps and a completely stereo-controlled fashion from the cis-1,2-dihydrocatechol 3. The starting material is a readily available and enantiopure compound that can be obtained in large quantity ia toluene dioxygenase (TDO) mediated dihydroxylation of iodobenzene.

Compound 1, the structure of which has been assigned to the marine natural product haliclorensin, was prepared by an unambiguous synthetic pathway and subjected to spectroscopic analysis. The derived data do not match those reported for the natural product.

The title compounds 1 and 2, which are effective and specific inhibitors of phosphohexomutases, have been prepared in enantiomerically pure form from toluene. The initial step of the reaction sequence involves enzymatic cis-1,2-dihydroxylation of toluene by E. coli JM109 (pDTG601) to give the cis-1,2-dihydrocatechol 3. The latter compound is then converted, ia a series of chemical oxidation and reduction steps, into compounds 1 and 2. The X-ray crystal structures of the bis-acetonide derivatives 11, 13 and 14 have been determined.

The marine natural products (±)-longamide (1), (±)-longamide B methyl ester (2), (±)-longamide B (3) and (±)-hanishin (4), each of which embodies a pyrroloketopiperazine core, have been synthesised in a concise fashion from pyrrole.