The use of cyclic monoterpenoids as enantiopure starting materials in natural product synthesis

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Chiral monoterpenoids are included in the large number of chiral starting materials (the so-called chiral pool) used in natural product synthesis. Not all of these compounds are available in both enantiomeric forms; however, this limits their versatility as chiral starting materials. Readily available chiral monoterpenoids are valuable and versatile starting materials for the enantiospecific synthesis of natural products and their widespread use in this respect is illustrated by the many successful syntheses. Although camphor is commercially available in both enantiomeric forms, (−)-camphor is approximately five to ten times more expensive than (+)-camphor. Fortunately, (−)-camphor can be prepared by oxidation of commercially available (−)-borneol with relatively inexpensive oxidizing agents. The versatility of (+)-camphor and (−)-camphor as enantiopure starting materials in natural product synthesis is because of the fact that the camphor structure can be functionalized regiospecifically. This chapter summarizes of the methods available for the regiospecific functionalization of camphor.

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