The Biomimetic Synthesis of (-)-Kaur-16-en-19-oic Acid

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The biomimetic total synthesis of (-)-kaur-16-en-19 oic acid will be attempted enantioselectively via a cation olefin polyannulation reaction. Chirality will be introduced by enantioselective epoxide formation via Sharpless asymmetric epoxidation. The key reaction will create three carbocycles and five contiguous stereocenters simultaneously in a single concerted reaction step and is expected to produce high enantioselectivities in the product molecule. The target is a natural product that has biological activity similar to gibberelines a plant growth hormone. It is often isolated from various plant species along with gibberellines, and may be an intermediate in gibberellin biosynthesis. The proposed synthesis improves upon published synthesis by Stereoselective strategies that will support a successful synthesis of the target compound. It is anticipated that a successful completion of the proposal will allow for the development of a general method of access that is modifiable for other diterpenoid natural product targets related to (-)-kaur-16-en-19-oic acid that possess more significant (i.e. anti- microbial, trypansomicidal and anti-HIV) biological activity.