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(+ )-Altholactone [(+)-1] is a dihydropyranone type acetogenin first isolated from the bark of a low shrub Polynalthia sp. in 1977. 1) This compound was also isolated as goniothalenol from the bark of the Annonacea plant, Goniothalamus giganteus, and showed antitumor activity against a leukemia mouse in vivo.2 Until now, 1 was found from various Goniothalamus species including Isoaltholactone (2). 2, 4) This biological activity and the unique structure led many chemists to synthesize 1 and its diastereomers. 5-12) However, there is no report for the synthesis of 3a, 7a-trans-epimers. To investigate the further biological activity including this point, we began to synthesize stereoisomers of 1. In this paper, we report the synthesis of (-)-ent-1, ( )-ent-2, (+)-7a-epi-1 and (-)-7a-epi-2 from 2, 3-0-cyclohexylidene-D-glyceraldehyde.

nippon nōyaku gakkaishi

Synthesis of (-)-&lt;i&gt;ent&lt;/i&gt;-Altholactone, (+)-7a-&lt;i&gt;epi&lt;/i&gt;-Altholactone, (-)-&lt;i&gt;ent&lt;/i&gt;-Isoaltholactone and (-)-7a-&lt;i&gt;epi&lt;/i&gt;-Isoaltholactone from 2, 3-&lt;i&gt;O&lt;/i&gt;-Cyclohexylidene-D-glyceraldehyde