Transcription of Multi-step Organic Synthesis
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Multi-step Organic Synthesis
8 Lecture Supplement: Multi-step Organic SynthesisMulti- step Organic SynthesisConversion of existing molecules into other useful sources: petroleum natural gas natural productsCommercial sourcesEtc. PharmaceuticalsPolymersGasolineTextilesE tc. Little molecules ----> big molecules Synthesis of unnatural products Modification of existing structures Synthesis of rare and useful natural productsExample: Paclitaxel (taxol): anticancer drug and rare natural productOHOOOOOOOHHHOHOHONHHOPhOHOE xample #2: Synthesis of indynaprost from cyclopentadieneintoOHHHOHOHO2 CCyclopentadieneIndynaprost(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 /deprotectionKeys 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 stepfrom where I am?
⇒ 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
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