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Pauwels, Peter Jean Stephen (1962) Chemistry of lignans. Doctoral thesis, Sir John Cass College.
A review of reactions of lithium aluminium hydride having a bearing on the suitability of the reagent for reducing lactonic lignans is made.
The reduction of podophyllotoxin by lithium aluminium hydride is discussed, and evidence is presented to show that it proceeds stereospecifically to give an optically active triol. Reduction of picropedophyllin and epipodophyllotoxin, two epimers of podophyllotoxin, has been achieved.
The three triols have been dehydrated to compounds shown to have a tetrahydrofuran ring in their structure. Evidence is presented to show that the compound derived from podophyllotoxin contains a 1,3 tetrahydrofuran ring.
Attempts have been made to prepare derivatives of the triols and their dehydration products, but without success. Iso-Propenyl acetate, in its action as an acetylating agent, is discussed. The formation of the first known compound having an α-apopodophyllotoxin structure is reported.
The results obtained in an earlier investigation into the reduction of podophyllotoxin and picropodophyllin are examined and shown to be erroneous in the case of podophyllotoxin.
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