α -Santonin, isolated from the flower heads of certain species of Artemisia , is an anthelmintic (meaning against intestinal worms). This terpene is used in oral doses of 60 mg to rid the body of roundworms such as Ascaris lumbricoides . It has been estimated that over one-third of the world’s population is infested with these slender, threadlike parasites. (a) Locate the three isoprene units in santonin and show how the carbon skeleton of farnesol might be coiled and then cross-linked to give santonin. Two different coiling patterns of the carbon skeleton of farnesol can lead to santonin. Try to find them both. (b) Label all chiral centers in santonin. How many stereoisomers are possible for this molecule? (c) Calculate the index of hydrogen deficiency for santonin.

BuyFind

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
BuyFind

Organic Chemistry

8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350

Solutions

Chapter
Section
Chapter 5, Problem 5.33P
Textbook Problem

α-Santonin, isolated from the flower heads of certain species of Artemisia, is an anthelmintic (meaning against intestinal worms). This terpene is used in oral doses of 60 mg to rid the body of roundworms such as Ascaris lumbricoides. It has been estimated that over one-third of the world’s population is infested with these slender, threadlike parasites.

Chapter 5, Problem 5.33P, -Santonin, isolated from the flower heads of certain species of Artemisia, is an anthelmintic

  1. (a) Locate the three isoprene units in santonin and show how the carbon skeleton of farnesol might be coiled and then cross-linked to give santonin. Two different coiling patterns of the carbon skeleton of farnesol can lead to santonin. Try to find them both.
  2. (b) Label all chiral centers in santonin. How many stereoisomers are possible for this molecule?
  3. (c) Calculate the index of hydrogen deficiency for santonin.

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Chapter 5 Solutions

Organic Chemistry
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