The optical resolution of (±)-7-endo-oxabicyclo [2.2.1] hept-5-ene-2-carboxylic acid (±)-(1) has been accomplished by use of (R)-(+)- and (S)-(-)-α-methylbenzylamine, respectively. The absolute configuration of (-)-(1) has been determined on the basis of X-ray analysis of the bromo lactone (2) derived from it. The title branched-chain cyclitol (6), the antibiotic produced by Streptomyces sp. MA-4145, has been totally synthesized from (-)-(1), its absolute configuration being established. Synthesis of the penta-N,O-acetyl derivative (12) of (+) -validamine, the branched-chain aminocyclitol obtained by degradation of the antibiotic validamycin A, has also been carried out from (-)-(1).
|Number of pages||4|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 1985 Jan 1|
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