Question & Answer: Provide the needed starting material, reagents, or products for each step of the overall…..

1) Roadmaps. Provide the needed starting material, reagents, or products for each step of the overall synthesis problems below. /4 /4 27 /4 MCPBA Dispalune(sex phermone of the gypsy moth) /4 /4 /4 2) H,O C,H20, 1) BH,. THI 2) H2O, Nal α-Milisriatin (an insect pheromone) CjoH2o0, /4 Hint enolate CHO /4 chemistry fron 4 chapter 22 /40

Provide the needed starting material, reagents, or products for each step of the overall synthesis problems below.

Expert Answer

1. Please check the attached figure. Initially, acetylene upon treatment with n-BuLi and decyl bromide gives compound A. Compound A upon treatment with n-BuLi and alkyl bromide gives compound B. Now alkyne group in compound B can be reduced to alkene using Lindler catalyst (Pd partially poisoned with quinoline) to give Cis-alkene C which further oxidation with mCPBA gives epoxide D.

On the other hand, aldehyde upon treatment with methyl Grignard gives alcohol E which upon oxidation gives ketone F. The 1-carbon Wittig olefination gives alkene G. Now compound G, upon treatment with borane.THF followed by H2O2/NaOH gives primary alcohol H which upon reaction with TsCl and base gives corresponding tosylate (K) The tosylate can be displaced with enolate ion gives ketone I which on acidic hydrolysis deprotects acetal and gives diol J. Under the similar condition, compound J will be cyclized again to give our final compound.

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