本論文共分為兩部分，分別為 (1) 天然物 viridn 的合成研究；(2) 天然物 wortmannin 的合成研究。
第一部分，我們以分子內的自由基環化反應及合環歧化反應做為合成的關鍵步驟來合成天然物 viridin 的關鍵中間體化合物26。我們以文獻報導的化合物29為起始物，經過氧化反應、碘化反應、烷基化反應合成出化合物28，於低溫下進行分子內自由基環化反應而得化合物41a和41b，再將兩者進行芳香化反應而得化合物27，最後在催化劑33的作用下進行合環歧化反應得到關鍵中間體化合物26，由化合物29到化合物26我們一共採用9個步驟，總產率為10.7％。
第二部分，我們以分子內的自由基環化反應及羥基-羧酸間的縮合反應為關鍵步驟來合成天然物 wortmannin 的關鍵中間體化合物32。我們以化合物36為起始物，經過還原掉頭反應、羥基保護、氧化反應、碘化反應、烷基化反應合成出化合物61，以本實驗室發展的分子內自由基反應可得化合物62，進行雙鍵遷移、氧化反應後可得化合物64，預計再進行去保護、縮合反應後即可得關鍵中間體化合物32，我們目前採用了13個步驟，總產率為4.5％。

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%.

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