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Title: New strategy for diene synthesis : application in total synthesis of Palmerolide A
Authors: Wen, Zhenkang
Keywords: DRNTU::Science::Chemistry
Issue Date: 2012
Source: Wen, Z. (2012). New strategy for diene synthesis : application in total synthesis of palmerolide A. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: Palladium-catalyzed alkenylation offers one of the most efficient methods for the synthesis of functionalized butadienes. However, due to the need for pre-functionalization of reactants and undesirable formation of stoichiometric amount of waste in the reactions, these processes were rendered neither atom-economical nor environmentally benign. The emphasis of this thesis is focused on the design and development of a palladium-catalyzed cross-coupling reaction of unactivated alkenes with acrylates for the construction of 1,3-diene motifs and its application towards a total synthesis of the natural product, Palmerolide A. In the first introduction chapter, a summary of established methodologies in the construction of 1,3-butadiene system is outlined, ranging from carbonyl olefination to recently emerging olefin metathesis. In particular, the strategy of transition metal-catalyzed alkenylation is thoroughly and intensively discussed. With the increasing demand for more atom- and step-economical methods, we have developed a direct and efficient palladium-catalyzed method for the cross-coupling of homoallylic and allylic alcohols with acrylates that produces dienic alcohols in moderate to high yields, and with good stereoselectivity.
DOI: 10.32657/10356/51110
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Theses

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