Total synthesis of amaminol A

This thesis includes an extensive review of preparation of bicyclo[4.3.0]nonane derivatives. Bicyclo[4.3.0]nonanes can be prepared by several methods. The most important preparation method of bicyclo[4.3.0]nonanes is intramolecular Diels-Alder cycloaddition (IMDA). Several biologically active natural and unnatural compounds contain bicyclo[4.3.0]nonanes in their molecular framework. The synthetic efforts toward natural compounds such as pulo'upone, isopulo'upone, indanomycin, stawamycin, cochleamycin A, ikarugamycin and lepicidin A are surveyed in this thesis. The second part of the review includes preparation methods for bicyclo[4.3.0]nonane derivatives. The synthesis part of this thesis presents my own results of synthetic efforts on amaminol A. Amaminol A was obtained as the side product from the synthesis of amaminol A diastereomer. Although amaminol A was obtained as the side product, the developed route allows the preparation of amaminol A as the major product by changing the stereochemistry of the employed organocatalyst. The bicyclo[4.3.0]nonane part of amaminol A was obtained utilizing two different types of IMDA's. These were chiral auxiliary induced and organocatalytic IMDA cycloadditions. Many active organic molecules include vicinal amino alcohol moieties in their molecular framework. The preparation of vicinal amino alcohols from α-amino ketones was also studied in this thesis. Chelation type reduction was found to give the highest diastereoselectivities with N-tert-butylcarbamate protected α-amino ketone.reviewe