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Gary Willman
Albright College

Subject Listing - Chemistry
Advisor: Dr. Christian Hamann

Thursday, Oral Session 1, Presentation 5, Karpen Hall 038

CONTINUED PROGRESS TOWARD THE SYNTHESIS OF (-)-TETRANORLABDANE OXIDE FROM ABIETIC ACID

(-)-Tetranorlabdane oxide is an extremely valuable fixative used by the perfume industry that was formally produced from a natural product of the sperm whale (Physeter macrocephalus) called Ambergris. Due to environmental concerns, Ambergris is now banned for use in many industrial countries, including the United States. The perfume industry had to devise a synthetic way of making this valuable natural product. Today, (-)-tetranorlabdane oxide is currently synthesized by the perfume industry by one synthetic pathway with (-)-scarelol as the starting material. This production cost of (-)-tetranorlabdane oxide from (-)-scarelol is very high, which is passed on to the consumer. The high demand of (-)-tetranorlabdane oxide on the international market also contributes to the high cost of perfumes containing (-)-tetranorlabdane oxide.

We are reporting on the progress of synthesizing (-)-tetranorlabdane oxide from abietic acid, which is a naturally occurring product found in pine rosin. We have successfully isolated gram quantities of abietic acid from pine rosin. The first six steps of the proposed synthetic pathway been successfully completed and their products analyzed. We also propose future steps in the synthetic pathway that will eventually lead to the product, (-)-tetranorlabdane oxide.

Advisor: Dr. Christian Hamann, Associate Professor of Chemistry, Chemistry and Biochemistry, Albright College, Reading, PA