Materials and General Methods

Commercial reagents and solvents were used without additional purification, unless otherwise noted. 3-cyclopentylpropanoic acid, cyclobutanemethanol, ethyl 2-cyclohexylacetate, 2-(2-bromoethyl)-1,3-dioxolane, 4-ethylcyclohexanone were purchased from Alfa Aesar. Cycloheptanecarboxylic acid was purchased from Frinton Labboratories, Inc. 7-octen-1-ol and 6-hepten-1-ol were purchased from TCI America. Ether and THF were dried and distilled from Na/benzophenone. Analytical thin layer chromatography (TLC) was performed on precoated silica gel 60 plates. Column Chromatographic purifications were performed using 230-400 mesh silica gel from Alfa Aesar. Spectral Characterization 1H NMR spectra were obtained at 300 MHz. Chemical shifts are reported in parts per million (ppm) referenced to the appropriate solvent peak. The following abbreviations were used to describe peak patterns when appropriate: br = broad, s = singlet, d = doublet, t =triplet, q = quartet, m = multiplet, dd = doublet of doublet, dt = doublet of triplet. Coupling constants, J, are reported in Hertz (Hz). 13C NMR were recorded at 75 MHz. Infrared (IR) spectra were recorded using a Thermo Nicolet 6700 FT-IR Spectrometer. GC/MS analyses of 4 and 11, and all other GC analyses, were performed on a Shimadzu GC/MS QP5000 with GC-17A Gas Chromatograph (capillary column: DB-1-30N-STD). Temperature programs for GC analysis: Program1: held at 50 °C for 1min, heated from 50 to 150 °C at 3 °C/min, and held at 150 °C for 4min; program 2: held at 60 °C for 1min, heated from 60 to 150 °C at 4 °C/min, and held at 150 °C for 4 min. Mass spectra for compounds 9, 2a, 11a, 14 and 15 were recorde