sungkyunkwan university The Logic of Chemical Synthesis - E.J. Corey and X-M. Cheng - 교과목 : 약품합성화학 수강대상 : 약학부 4 년 수강학기 : 2007 학년도 1 학기

The Basis for Retrosynthetic Analysis sungkyunkwan university 1. Multistep Chemical Synthesis Due to an astronomical number of discrete carbogens, differing in number and type of constituent atoms, in size, in topology and in three dimensional (stereo-) arrangement, the construction of specific molecules by a single chemical step from constituent atoms or fragments is almost never possible even for simple structures. Efficient synthesis, therefore, requires multistep construction process which utilize at each stage chemical reactions that lead specifically to a single structure.

Retrosynthetic Analysis sungkyunkwan university Retrosynthetic analysis is a problem-solving technique for transforming the structure of a synthetic target (TGT) molecule to a sequence of progressively simpler structure along a pathway which ultimately leads to simple of commercially available starting materials for a chemical synthesis.

Transforms and Retrons sungkyunkwan university In order for a transform to operate on a target structure to generate a synthetic predecessor, the enabling structural subunit or retron for that transform must be present in the target.

Transforms and Retrons sungkyunkwan university 2, 3, and 4 can be regarded as a partial retrons for D-A Tf.

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Types of Transforms sungkyunkwan university The most crucial tranforms: 1. simplifying transforms - disconnecting molecular skeleton (chains (CH) or rings (RG)) - removing or disconnecting functional groups (FG) - removing or disconnecting stereocenters (ST) 2. non-simplifying transforms - connecting or rearranging molecular skeleton - interchanging or transposing functional groups (FGI or FGT) - Inverting or transferring stereocenters

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FGI Transforms sungkyunkwan university FGT Transforms

Rearrangement Transforms sungkyunkwan university FGA Transforms

Stereocenters Transforms sungkyunkwan university Synthesis of (-)-Lentiginosine Y.H. Jung et. al. Org. Lett. 2006, 8,

sungkyunkwan university Figure 1. Proposed reaction mechanism of cinnamyl polybenzyl ethers 6 and 9 with CSI. Y.H. Jung et. al. Org. Lett. 2006, 8,

1. Tranform-Based Strategies sungkyunkwan university Diels-Alder Cycloaddition as T-Goal - Retrosynthetic analysis of Fumagillol - Retrosynthetic analysis of Ibogamine - Retrosynthetic analysis of Estron

Retrosynthetic analysis of Fumagillol sungkyunkwan university

Retrosynthetic analysis of Fumagillol sungkyunkwan university

Synthesis of Fumagillol sungkyunkwan university

Synthesis of Fumagillol sungkyunkwan university

Retrosynthetic analysis of Ibogamine sungkyunkwan university

Retrosynthetic analysis of Estrone sungkyunkwan university

2. Enantioselective Transforms as T-Goals sungkyunkwan university Sharpless Asymmetric Epoxidation

Enantioselective Transforms as T-Goals sungkyunkwan university

3. Mechanistic Transform Application sungkyunkwan university

4. T-Goal Search using Tactical Combinations of Transforms sungkyunkwan university

4. T-Goal Search using Tactical Combinations of Transforms sungkyunkwan university