Two novel monomers, ambrettolide epoxide and isopropyl aleuriteate, encompassing functional groups, were obtained in a single step from commercially available materials. Novozym 435 catalyzed ring opening polymerization of ambrettolide epoxide furnished a polymer of M-n = 9.7 kg/mol and PDI = 1.9 while the epoxide groups remained unaffected during the polymerization. Selective polymerization of the primary hydroxyl groups of isopropyl aleuriteate using Novozym. 435 was feasible and a polymer with moderate molecular weight (M-n = 5.6 kg/mol, PDI = 3.2) was isolated in moderate yield (43%). Subsequently, copolymerization of isopropyl aleuriteate with E-CL in different ratios was performed, resulting in soluble, hydroxy functional polymers with good molecular weights (M-n = 10.4-27.2 kg/mol) in good yield (71-78%). The secondary hydroxy groups in the polymer reacted easily with hexyl isocyanate, showing the potential of isopropyl aleuriteate as a comonomer for the synthesis of functional polyesters. (c) 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 5968-5978, 2007.