a. The following is a real synthetic reaction published by the Burns lab at Stanfordtowards the synthesis of complex ‘ladderane' bacterial phospholipids. In thepresence of a copper triflate catalyst (not important for the question) and 254 nmlight, two major pericyclic products are formed at -4°C. List if each product isformed under thermal or photochemical conditions and show the relevantmolecular orbital for the electrocyclization reaction on the right side.HH5 mol%(CuOTf)2 C6H6-4 °C, C₂H6254 nmthermal (heat) orphotochemical (light)pericyclic reaction?37%ΗΗΗΗΗΗΗΗ42%relevant molecular orbital forelectrocyclization reaction:b. Draw a mechanism for the following [3,3] sigmatropic rearrangement.c. Use the starting ketone material on the left and any other reagents/solvents ofyour choosing to synthesize the ester molecule on the right. Number your chemicalsteps sequentially and please show intermediates after each step towards yourfinal product. You do not need to show mechanisms for this question.

The Q has 3 subparts, showing 3 reaction conditions Subpart a is the reaction of…

a. The following is a real synthetic reaction published by the Burns lab at Stanford towards the synthesis of complex 'ladderane' bacterial phospholipids. In the presence of a copper triflate catalyst (not important for the question) and 254 nm light, two major pericyclic products are formed at -4°C. List if each product is formed under thermal or photochemical conditions and show the relevant molecular orbital for the electrocyclization reaction on the right side. H 5 mol% (CuOTf) ₂ C6H6 -4 °C, C6H6 254 nm thermal (heat) or photochemical (light) pericyclic reaction? 37% ΗΗΗΗ HHHH 42% relevant molecular orbital for electrocyclization reaction: b. Draw a mechanism for the following [3,3] sigmatropic rearrangement. c. Use the starting ketone material on the left and any other reagents/solvents of your choosing to synthesize the ester molecule on the right. Number your chemical steps sequentially and please show intermediates after each step towards your final product. You do not need to show mechanisms for this question. ix

a. The following is a real synthetic reaction published by the Burns lab at Stanford towards the synthesis of complex 'ladderane' bacterial phospholipids. In the presence of a copper triflate catalyst (not important for the question) and 254 nm light, two major pericyclic products are formed at -4°C. List if each product is formed under thermal or photochemical conditions and show the relevant molecular orbital for the electrocyclization reaction on the right side. H 5 mol% (CuOTf) ₂ C6H6 -4 °C, C6H6 254 nm thermal (heat) or photochemical (light) pericyclic reaction? 37% ΗΗΗΗ HHHH 42% relevant molecular orbital for electrocyclization reaction: b. Draw a mechanism for the following [3,3] sigmatropic rearrangement. c. Use the starting ketone material on the left and any other reagents/solvents of your choosing to synthesize the ester molecule on the right. Number your chemical steps sequentially and please show intermediates after each step towards your final product. You do not need to show mechanisms for this question. ix

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter24: Catalytic Carbon-carbon Bond Formation

Section: Chapter Questions

Problem 24.36P

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