Approaches toward the synthesis of natural product Viridin and Wortmannin

• Main Author: 林景宏
• Other Authors: 沙晉康
• Format: Others
• Language: zh-TW
• Published: 2005
• Online Access: http://ndltd.ncl.edu.tw/handle/25389514894114530076

博士 === 國立清華大學 === 化學系 === 93 === There are two parts in this thesis, including (1) the synthesis toward the natural product viridin, (2) the synthesis toward the natural product wortmannin. In the first part, we utilize the intramolecular radical cyclization and ring closing metathesis as the key steps toward the crucial intermediate compound 26. We choose the compound 29 published in the paper as the starting material, via oxidation reaction, iodination reaction, alkylation reaction to afford the compound 28. We furnish compound 41a and 41b by intramolecular radical cyclyzation at low temperature. Further aromatization to obtain compound 27. Finally, we attain the critical intermediate compound 26 via the ring closing metathesis catalyzed by the Grubbs reagent 33. We adopt nine steps from compound 29 to compound 26 and the total yield is 10.7%. In the second part, we utilize the intramolecular radical cyclization and hydroxy-acetic acid condensation as the key steps toward the crucial intermediate compound 32. We select the compound 36 as the starting material, via reduction reaction, acidic elimination reaction, oxidation reaction, iodination reaction, alkylation reaction to afford the compound 61. To attain the compound 62 by intramolecular radical cyclization developed in our labrotory. We furnish compound 64 after double bond migration reaction, oxidation reaction. We presume further deprotection reaction, condensation reaction to obtain critical compound 32. We so far take the thirteen steps and the total yield is 4.5%.