Indolizomycin is a potent antibiotic agent produced by a microorganism called SK2-52. Of particular interest is the fact that SK2-52 is a mutant microorganism that was created in a laboratory from two different strains, Streptomyces teryimanensis and Streptomyces grisline, neither of which is antibiotic producing. This raises the possibility of using mutant microorganisms as factories for producing novel structures with a variety of medicinal properties. During S. J. Danishefsky’s synthesis of racemic indolizomycin, compound 1 was treated with triphenylphosphine (PPh3) to afford compound 2 (J. Am. Chem. Soc. 1990, 112, 2003–2005). The reaction between 2 and 3 then gave compound 4. These processes are believed to proceed via the following intermediates. Complete the mechanism by drawing all curved arrows and identify the arrow-pushing pattern employed in each step.
Frequently Asked Questions
What scientific concept do you need to know in order to solve this problem?
Our tutors have indicated that to solve this problem you will need to apply the Reaction Mechanism concept. You can view video lessons to learn Reaction Mechanism. Or if you need more Reaction Mechanism practice, you can also practice Reaction Mechanism practice problems.
What is the difficulty of this problem?
Our tutors rated the difficulty ofIndolizomycin is a potent antibiotic agent produced by a mic...as high difficulty.
What professor is this problem relevant for?
Based on our data, we think this problem is relevant for Professor Daoudi's class at UCF.
What textbook is this problem found in?
Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.