Juvabione and its Analogs. Juvabione and Δ4′ -Dehydrojuvabione Isolated from the Whole Wood of Abiesbalsamea, have the R,R Stereoconfigurations, not the R,S

Abstract

The petroleum ether soluble fractions from the whole wood meal of a number of native Abiesbalsamea (L.) Mill. var. balsamea and var. phanerolepis Fern. contain varying amounts of several juvabione analogs. These include the previously reported (+)-juvabione (1a), atlantones (2), and lasiocarpenone (3). This paper describes the first isolation of (+)-Δ4′-dehydrojuva-bione (R,R) (5a) and proves the R,R stereoconfiguration for (+ )-juvabione (1a) isolated from native Abiesbalsamea. These results require that those samples previously isolated from a Slovak fir and which have the R,S stereoconfigurations, be renamed (+ )-epijuvabione (6 ) and (+ )-Δ4′-dehydroepijuvabione (7).