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CEM 3005 Tutorial Natural Products and Organoanalytical Chemistry

August 2013

1) Present steps (with mechanisms) for each of the dotted arrows in the following natural product biosynthesis. Which class does each one belong to? a)

b)

c) For Boldine, a benzylisoquinoline alkaloid: i) Use a phenol oxidative coupling (following some selective methylations) to cyclize to the key intermediate shown, and ii) a 1,2-rearrangement involving a carbocation (Wheland-like) to transform to the natural product.

2 2) Assign a class of natural product (fatty acid, polyketide, alkaloid, terpene or steroid) to each of the following natural products, explaining the biosynthetic source:

3) Present a protocol for chemical separation of each of the following: a)

b)

4) Present structures for the following: a) Hint: Note resonance at ~ 205 ppm in 13C NMR spectrum + IR

b) Hint: Take note of IR

RH