Synthesis of 2(S)-2-(undec-4-enoylamino)propyl-undec-4-enoate (alaninol diene) (2).

 To a stirred solution of undecenyl acid (5.0 g, 2.7 x 10 -2 mmol) in 50 mL CHC13

was added R-alaninol (0.95 g, 1.3 x 10-2 mmol); 1,3-diisopropylcarbodiimide (DIC) (4.23

mL, 2.7 x 10-2 mmol); and 4-(dimethylamino)pyridine (DMAP) (0.26 g, 2.16 mmol) at 25

C in a 100 mL round bottom flask under an argon atmosphere. The reaction was

allowed to stir for 24 hours. The mixture was filtered to remove urea salts and the

remaining organic solution was washed successively with 1 M HC1 (2 x 20 mL);

saturated NaHCO3 solution (2 x 20 mL); and saturated NaCl solution (1 x 20 mL). The

organic layer was dried over MgSO4 overnight. The solution was filtered and the solvent

and volatile small molecules were removed from the washed organic layer by vacuum

evaporation resulting in a viscous oil. Upon cooling, the solid was recrystalized once

from ethyl acetate and hexane, and twice from methanol and water. Overall yield for the

resulting monomer (2) was 11%. 1H NMR (300 MHz, CDC13, ppm): 6 1.15-1.20 (m,

5H), 1.20-1.44 (m, 22H), 1.54-1.68 (s, 5H), 1.98-2.09 (q, 4H), 2.11-2.18 (t, 2H), 2.28-

2.38 (t, 2H), 3.94-4.18 (m, 2H), 4.22-4.36 (q, br, 1H), 4.86-5.08 (m, 4H), 5.6 (d, br, 1H),

5.72-5.90 (m, 2H). 13C NMR (75 MHz, CDC13, ppm): 6 17.64, 25.12, 25.90, 28.02,

29.08, 29.26, 29.49, 33.97, 34.37, 37.09, 44.52, 66.92, 114.32, 139.28, 172.72, 174.14.

Elemental Analysis (C,H,N): Theoretical: (73.66, 11.13, 3.44). Found: (73.25, 11.13,

3.37). EI/HRMS [M + 1]: Calculated for C25H45N03: 408.3399 g/mol. Found:

408.3483.

Synthesis of 2(S)-3-methyl-2-(undec-4-enoylamino)butyl-undec-4-enoate (valinol
 diene) (3).

 To a stirred solution of undecenyl acid (5.0 g, 27 mmol) in 50 mL CHC13 was

added L-valinol (1.30 g, 12.6 mmol); 1,3-diisopropylcarbodiimide (DIC) (4.23 mL, 27