Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/15145
Title: Part 1: Synthetic studies towards the total synthesis of tedanolide Part 2: Studies on indium-mediated allylation of secondary allylic bromides
Authors: WONG CHEK MING
Keywords: synthetic studies, tedanolide, aldol reaction, indium, allylation, allylic
Issue Date: 22-Dec-2005
Source: WONG CHEK MING (2005-12-22). Part 1: Synthetic studies towards the total synthesis of tedanolide Part 2: Studies on indium-mediated allylation of secondary allylic bromides. ScholarBank@NUS Repository.
Abstract: PART 1 : Synthetic Studies Towards The Total Synthesis Of TedanolideThe key fragments in the synthetic studies toward the total synthesis of tedanolide, the C1-C12 diketoester and C13-C23 aldehyde were obtained in satisfactory yields and efficiency. Investigation of their union by aldol reaction revealed that these two fragments were synthetically viable for assembling the C1-C23 carbon backbone of tedanolide. A stereoselective route to both the desired diastereomer representing the carbon framework of tedanolide and the undesired diastereomer representing its C13-epimera??s carbon skeleton was achieved by the use of chiral boron reagents. PART 2 : Studies On Indium-Mediated Allylation of Secondary Allyic BromidesPreliminary investigation using the secondary allylic bromide (3-Bromo-1-phenylbut-1-ene) was preformed to study the allylation reaction mediated by indium metal. Both the I?-adducts and the I?-adducts were obtained in good regio- and diastereoselectivity in the allylation using this bromide. The I?-anti-Z-adducts was obtained predominantly over the I?-anti-E-adducts and I?-syn-Z or I?-syn-E-adducts in the I?-regioselective allylation reaction. The I?-syn-E-adducts were favored over the E-I?-anti adducts in the I?-regioselective allylation reaction.
URI: http://scholarbank.nus.edu.sg/handle/10635/15145
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