A 5-membered INOC cycloadduct 84 was employed to prepare alcohol 91, which was transformed into several cyclopent-2-enone derivatives 94-96. / By using intramolecular nitrile oxide-alkene cycloaddition (INOC) as the kep step to construct hydroxylated carbocycles, gabosine F was synthesized for the first time from L-arabinose. Hence, theoretically, gabosine B, which is the enantiomer of gabosine F, can also be synthesized from D-arabinose by the same synthetic strategy. / In this thesis, the background information on the construction of carbocycles from carbohydrates via intramolecular 1,3-dipolar cycloaddition is presented. A review regarding the syntheses of gabosine B and cocaine are also descibed. / Starting with D-ribose, INAC of nitrones 113, 129, and 140, bearing an alpha/beta-unsaturated ester as the dipolarophile was studied. The INAC endo-cycloadduct 141 (cycloheptane) was converted into natural cocaine sucessfully, together with cocaine analogues 162,169,170,173,175, and 177. / The regioselectivity of intramolecular nitrone-alkene cycloaddition (INAC) was studied. The INAC of hept-6-enose nitrone 98, with a 3,4- trans-pentylidene acetal as the only blocking group, afforded endo-cycloadduct 97 (cycloheptane) exclusively. This result concluded that the regiospecific outcome of this INAC reaction is due to the present of the 3,4-trans-pentylidene acetal blocking group. / To investigate the regioselectivity in INAC of hex-5-enose with a 2,3- trans-pentylidene acetal blocking group, nitrones 178 and 195 were prepared from D-mannitol. endo-Cycloadducts (cyclohexanes) were afforded exclusively. / So, King Ho. / Adviser: Kung Ming Tony Shing. / Source: Dissertation Abstracts International, Volume: 73-06, Section: B, page: . / Thesis (Ph.D.)--Chinese University of Hong Kong, 2011. / Includes bibliographical references (leaves 165-171). / Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Electronic reproduction. [Ann Arbor, MI] : ProQuest Information and Learning, [201-] System requirements: Adobe Acrobat Reader. Available via World Wide Web. / Abstract also in Chinese.