Defense Mechanisms of Arthropods. 84. Synthesis of (-)-α-Necrodol and (-)-β-Necrodol: Novel Cyclopentanoid Terpenes from a Carrion Beetle

Article abstract of DOI:10.1021/jo00300a021

Syntheses of (-)-α-necrodol (1) and (-)-β-necrodol (2) from (+)-phenylcamphoric acid (7a) are described.In addition, several related compounds, (+)-epi-α-necxrodol (3), (+)-epi-β-necrodol (4), and (+)-γ-necrodol (5), have been prepared.The absolute configuration of natural α-necrodol has been established as 3R,5R by comparison of its (+)-α-methoxy-α-(trifluoromethyl)phenylacetyl ester with the ester derived from synthetic 1.