Let me know in the comments below.You’re very welcome Mohamad.
We have been asked to do a retrosynthesis of (6S)-6-[(2S)-2-hydroxy-4-phenylbutyl]oxan-2-one J from 3-phenylpropan-1-ol K: My first instinct would be to do a functional group interconversion of the alcohol to a ketone, to then do a Baeyer-Villiger oxidation. If the carboxylic acid comes from an FC Alkylation, the alkyl group prior to oxidation is an We need one more reaction that is not apparent in the product.All these thoughts should quickly run through your head. oxidation of an alcohol gives an aldehyde, further oxidation a carboxylic acid. It’s much easier to think through theNow we treat the alkene as our new product and ask the same question again.Do I know of a reaction that will either carry out this transformation or get me close?Why absolutely yes, a simple elimination reaction as we’ve seen above.However, this time we can’t simply use a strong base because the pi bond will favor the more substituted and Zaitsev product 2-butene.Which reagent will carry out this ‘anti-Zaitsev’ or Hoffman elimination?But let’s not worry about tert-butoxide right now, instead let’s simply acknowledge the fact that we CAN react 2-chlorobutane to form 1-butene and draw this transformation.Once you have all of your intermediates drawn in from product to reactant, quickly follow the sequence from reactant to product to ensure it looks right and makes sense.Ask yourself this question one at a time as you fill in the reaction conditions and complete your retrosynthesis sequence.We start with a secondary halogen and form a less substituted pi bond.While some professors will accept this as is, others will require a full set of conditions.Let’s use potassium tert-butoxide dissolved in it’s own conjugate alcohol tert butanol and heat to help carry out this reaction. Click the image below to Learn my shortcut
<< /Length 8 0 R /Type /XObject /Subtype /Form /FormType 1 /BBox [0 0 612 792] /Resources 6 0 R /Filter /FlateDecode >> The synthetic and retrosynthetic analysis of alcoholic compounds are required for their utility.
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1,1 CC. << /ProcSet [ /PDF ] /XObject << /Fm1 5 0 R >> >> Tony: FC Alkylation adds just the alkyl (C+H) chain. FC Acylation will add a carbonyl. My goal is to make this topic less intimidatingOn the solution to the F.C. Retrosynthetic analysis . Carboxylic acid - Carboxylic acid - Synthesis of carboxylic acids: Most of the methods for the synthesis of carboxylic acids can be put into one of two categories: (1) hydrolysis of acid derivatives and (2) oxidation of various compounds. %��������� Give the retrosynthetic analysis for the following three compounds . 23 endstream That’s the key. Although FGI doesn't offer much gain to a synthesis, it sets the stage for subsequent disconnection of the intermediate. Looking closer to the amino alcohol 95 moiety, it could be prepared from indene 97.
Many organic transformations can be CO2H CO2H CO2H Answers: The first is the easiest; it is an !,"-unsaturated compound so we are looking at either aldol condensation or a simple Wittig reaction. If not, what happened to the C=O that was used in the first step? Ok, perhaps I’m exaggerating, your professor will hopefully limit your retrosynthesis problems to three to seven steps. It’s faster, more precise and has less competition (when conditions are set right.