Chapter 18: Q15P (page 942)
Propose a mechanism for each cyanohydrin synthesis just shown.
Chapter 18: Q15P (page 942)
Propose a mechanism for each cyanohydrin synthesis just shown.
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Get started for freeNMR spectra for two compounds are given here, together with the molecular formulas. Each compound is a ketone or an aldehyde. In each case, show what characteristics of the spectrum imply the presence of a ketone or an aldehyde, and propose a structure for the compound.
Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.
(a)
(b)
(c)
(d)
(e)
(f)
(g)
The family of macrolide antibiotics all have large rings (macrocycle) in which an ester is what makes the ring; a cyclic ester is termed as a lactone. One example is amphotericin B, used as an anti-fungal treatment of last resort because of its liver and heart toxicity. Professor Martin Burke of the University of Illnois has been making analogs to retain the antifungal properties but without the toxicity, including this structure published in 2015. (Nature Chemical Biology, (2015) doi: 10.1038/nchembio.1821). The carboxylate of amphotericin B has been replaced with the urea group (shown in red).
(a) Where is the lactone group that forms the ring?
(b) Two groups are circled. What type of functional group are they? Explain.
Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.
a.
b.
c.
d.
e.
f.
g.
h.
Question: Solving the following road-map problem depends on determining the structure of A, the key intermediate. Give structures for compounds A through K.
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