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Mother nature creates structurally diverse interesting secondary metabolites often with unexpected biological activity, but in scarce quantities. Target-oriented total synthesis provides access to such natural products in sufficient amounts for further exploration of bioactivity. In target-oriented total synthesis, there is a never ending demand for the development of new reaction methodologies in order to address challenges in the synthesis and also to improve current synthetic protocols. Taking this idea to heart, we have worked on novel asymmetric method development and applied some of the methodologies that we developed to total synthesis. This thesis is composed of five chapters. Chapter 1 provides a general introduction to the research work discussed in Chapter 2, 3 and 4. Also, the introduction at the beginning of each chapter discusses the relevant background of the research so as to provide sufficient understanding about the significance of the work and the results. Moreover, some of the research in chapters 2 and 3 was published in Org. Lett. in 2014 and rest of the work is from the manuscript which is currently in preparation. Also, the work disclosed in chapter 4 is published in Org. Lett. in full in 2015. Chapter 2 describes the development of a novel method for the synthesis of differentially protected chiral anti 1,2-diols via organomagnesium or organolithium addition to α-oxyaldehydes synthesized via organocatalytic oxidative incorporation of TEMPO. Excellent diastereoselectivity was observed in these reactions, regardless of the hybridization or presence or absence of branching of the incoming carbon nucleophile. Further attempts to access masked syn 1,2-diols using the same method via promoting

Catalytic enantioselective α,β,γ-trioxygenation and anti-1,2-diol from α-oxyaldehydes and its application in total synthesis of oxylipins isolated from Dracontium loretense