Total Synthesis Blog

This time short synthesis of racemic Cacalol:

This is a sesquiterpene isolated from the roots of Psacalium decompositum and it exhibit some interesting biological properties including antihyperglycemic, anti-inflammatory, antimicrobial and antioxidant activities. Authors of paper didn’t mention anything about biological activity of single enantiomers of Cacalol.

Retrosynthesis chart (not very good-looking…) is shown below:
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Back again! Today great and classic target: cholesterol (click on image to enlarge it).

When I was preparing to my summer Natural Product Exam and when I was admiring how Nature ‘do’ such big molecules by biosynthetic routes I just wanted to know how R. B. Woodward could synthesize such complex molecule like cholesterol. Well, it was more complicated than I expected. By the way – articles from 1950s are so difficult to read… there are no chemical equations and no schemes in some of them.

But let’s see how Woodward did his synthesis, but first let’s remind designation of steroids fused-ring system:

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