Extracts. An aliquot of each millipede crude extract was analyzed on GCMS using a RTX-5 column (30 m x 0.25 mm i.d. column) following an instrument method from 60 to 250 °C at 10°/min. Microhydrogenations were carried out by bubbling a slow stream of hydrogen through a small aliquot of the original extract, ca 50 μL, containing a few milligrams of PtO2 until the catalyst turned black. The supernatant was immediately subjected to GCMS analysis. Hydrogenation of extracts of both species gave two isomers of both 7-(4-methylpentyl)indolizidine ( ) and 2-(4-methylpentylquinolizidine ( ) in a 1:2 ratio (synthesis described below) ). In addition, the alkaloids in B. producta were hydrated by treating a small portion of the extract with 5% HCl in MeOH for 1 h at rt, at which point the mixture was carefully made basic with solid K2CO3 and extracted with 200 μL of diethyl ether. Analysis by GCMS showed the original 3 and 4 along with two new peaks with M + water adducts of 5 and 6. . A 1.6 M solution of n-butyllithium in hexane (1.0 mL) was added dropwise to a slurry containing 0.55 g (1.3 mmol) of 4-methylpentyltriphenylphosphonium bromide in 10 mL of THF under argon at 0 o C . The mixture was stirred for 0.5 h followed by the dropwise addition of 0.17 g (1.1 mmol) of 2-quinolizidone in 1 mL of THF and allowed to come to rt overnight . The mixture was filtered through celite and the solvent removed under pressure. The residue was triturated with 15 mL of anhydrous ether and filtered through a silica gel plug to provide 0.15 g of a 1:1 mixture of the starting 2-quinolizidone and a 1:1 mixture of (E and Z) isomers of 2-(4-methylpentylidine)octahydroquinolizidine with identical mass spectra: MS m/z (rel %) 221 (40, M + ), , 150 (100), 136 (48), 122 . This material was taken up in MeOH and treated with ca. 10 mg of PtO2 and a slow stream of hydrogen was bubbled through it until the catalyst turned black. After 20 min, the sample was filtered and the mixture analyzed on GCMS, which showed the presence of two isomers of 8 in a 12:1 ratio having identical mass spectra. Compound 8 is an amorphous colorless solid; EIMS m/z (rel %) 223 (43, M + ), .