3 Mycolipenic acid
questions
a.
b.
c.
d.
e.
f.
g.
h.
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j.
k.
l.
Give the name and draw the structure of TBDPS in compounds 5 - 11.
Give the name and draw the mechanism of the reaction 5 6.
Draw the enantiomere of the catalyst (S,RFe)-Josiphos
What would have been the product if (S,RFe)-Josiphos was used as a catalyst?
What would have been the product is no CuBr was added to the reaction of 5 ?? ?
How is a temperature of -78 °C obtained?
What is the meaning of “98% ee”? Give a complete explanation
In the reaction 6 7 (step 1) DIBAL-H was used. Draw the structure of this reagent.
What will be the product of this first step with DIBAL-H?
What is an HWE olefination? Provide the complete name of this reaction.
What reagent will have been used in this HWE olefination?
Below compound 8 is written “dr 45:1” What does the abbreviation “dr” stand for and draw
the structure of the minor compound (so the “1” in the ratio 45:1).
m. Give the name and draw the structures of the compounds TsCl and py (reaction 9 10)
n. Give the name of the reaction 9 10?
o. Give the mechanism of the reaction 10 11.
p. In the reaction 10 11, THF is used as a solvent. Give the name and draw the structure and
also provide the density and boiling point.
q. In the reaction 11 12, TBAF was used: Give the name and draw the structure of this reagent.
r. What type of reaction is reaction 12 13? Give the name of this kind of reaction.
s. Draw the mechanism of the reaction 13 + 14 15.
t. What type of reaction is reaction 15 3? Give the name of this kind of reaction.
u. What is the molecular formula (also called “brutoformule” in Dutch) of the final product
mycolipenic acid 3
v. What is the overall yield of the complete synthetic route 5 3?
LHD Jenniskens
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