Alkaloids are a class of nitrogen-containing natural products. Their tructural complexity and potent — Inorganic Chemistry Chemistry Question
Total Synthesis of Alkaloids
Alkaloids are a class of nitrogen-containing natural products. Their tructural complexity and potent biological activities has drawn attentions. Two representative examples are Sauristolactam and Pancratistatin.
Sauristolactam is known to have excellent cytotoxicity against various cancer cell lines. It could be prepared by following the synthetic sequence below.
10.1 Draw the structures of A – G.
Model Answer
SOLUTION
10.1 The structures of A – G:
Pancratistatin could be successfully synthesized via intermediates X1 and X2. The synthesis of these intermediates are shown in the attached scheme.
10.2 Draw the structures of A and B.
Model Answer
10.2 Scheme of the synthesis of Pancratistatin and structures of compound A and B:
10.3 Intermediate X1 (a single enantiomer with the stereochemistry shown) is labeled with deuterium with configuration as indicated below, propose the 3-D chair structure of compound E and the structure of compound F, with stereochemistry. Is Y a proton (1H) or a deuterium (2H)?
Model Answer
10.3 The structures of E and F