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Unformatted text preview: 8 Lecture Supplement: Multi-step Organic Synthesis Multi-step Organic Synthesis Conversion of existing molecules into other useful molecules. Natural sources: petroleum natural gas natural products Commercial sources Etc. →→→ Pharmaceuticals Polymers Gasoline Textiles Etc. • Little molecules ----> big molecules • Synthesis of unnatural products • Modification of existing structures • Synthesis of rare and useful natural products Example: Paclitaxel (taxol): anticancer drug and rare natural product O H O O O O O O OH H H O H OH O N H H O Ph O HO Example #2: Synthesis of indynaprost from cyclopentadiene into O H H HO HO HO 2 C Cyclopentadiene Indynaprost (Experimental platelet aggregation inhibitor) Lecture Supplement: Multi-step Organic Synthesis 9 Fundamental Synthesis Operations ⇒ C-C bond formation ⇒ functional group interconversions (FGI): • oxidation • reduction • substitution • elimination • addition • others ⇒ skeletal rearrangements ⇒ protection/deprotection Keys to Doing Synthesis Problems • Use reactions you know (flash cards) • Keep an eye on the requirements of the problem: Can I solve the problem in one step from where I am?...
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This note was uploaded on 03/09/2010 for the course CHEM 30B Chem 30B U taught by Professor Miguelgarciagaribay during the Summer '10 term at UCLA.
- Summer '10