SYNTHESIS OF (+)-5-EPI-ARISTOLOCHENE AND (+)-1-DEOXYCAPSIDIOL FROM CAPSIDIOL

Article abstract of DOI:10.1016/0031-9422(90)85100-T

(+)-5-epi-Aristolochene, a common precursor of the phytoalexins capsidiol and debneyol, was synthesized from capsidiol (ex.Capsicum annum) via (+)-1-deoxycapsidiol.It is identical (TLC, GC, GC-MS, ¹H NMR) with the enzymic product from cell-free preparations from elicitor-treated suspension cultures of Nicotiana tabacum incubated with either <1-¹⁴C>isopentenyl pyrophosphate or E,E-<1-³H2>farnesyl pyrophosphate.The (+)-1-deoxycapsidiol was identical (GC, MS, ¹³C and ¹H NMR) to a natural sample previously obtained from elicitor-treated fruits of C. annum.An isomer of 1-deoxycapsidiol, formed during the synthesis of this compound, was identified as 4-epi-eremophila-1(10),11-diene.