Abstract
Acyloin 6 and its acetate 7 were treated with zinc powder in acetic acid containing a trace of hydrochloric acid to yield unexpected ent-beyerane derivatives, 11 and 12. Diol 15 was oxidized to ketoaldehyde 16, which was subjected to Huang-Minlon modification of Wolff-Kishner reduction to give ent-15-kaurene( 4), ent-16-kaurene( 3), and ent-kaurane ( 17).
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