Question

identity the proton transfers

6.16 Indolizomycin is a potent antibiotic agent pro Group 2 - Identify the Proton Transfers interest is the fact that SK2-52 is a mutant microorganism ni antibiotic agent produced by a microorganism, called SK2-52. Of particular tam microorganism that was created in a laboratory from two one Sudins, Streptomyces teryimanensis and Streptomyces arisline, neither of which is an Taises the possibility of using mutant microorganisms as factories for product variety of medicinal properties. During S. J. Danishefsky was treated with triphenylphosphine (PPh3) to afford compound 2 compound 4. These processes are believed to proceed via mechanism by drawing all curved arrows, and identity the me, neither of which is antibiotic-producing. This as factories for producing novel structures with a ng S. J. Danishefsky's synthesis of racemic indolizomycin, compound phosphine (PPh3) to afford compound 2 5 The reaction between 2 and 3 then gave These processes are believed to proceed via the following intermediates. Complete the an curved arrows, and identify the arrow-pushing pattern employed in each step. Ph 6 :P-Pn Meo - ENEN Ph . MeO C Ố Meoc oppng 2 PPh Phyp-0- pho O Meoz Meo,c Meoc oo PPhe Meo C

Answer 1

Ans: The following Synthesis of racemic and indolizomycin Can --womitten using the Curved amous as- Hege P reach - loss of potential "Neuelesphilic fack from Pcrfae to hy leaving groupply N nucleophile t 3 genanation of N. Mele 2. No o opphz Nucleophilic attack forom negative Nantre I to Carebonyl centre. 09 ewe Meg mototine N'containing o lactone O es w ho ming lepphagne opening o m z ©PPh, OPPH₂ dining ro from below to epperside. (pedrawing of L 'Php MeocN transfert for pph Moup via p-o'bond fonmartier, Nucleophilic attack from imine functional goop.to 1 Carberry! centre leo and formation of 5-memben ming Helge elimination of poph group as a leaving goroup and generation of Carbonyl. Since Phoo phosphorous has a peators affinite towards Oxygen atom due to strong po' bord foormation so, proiviously p-N to p o bond formation favours and also the final p=0 formation is expected.