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課程名稱︰有機化學三
課程性質︰五選三必修
課程教師︰陸天堯
開課學院：理學院
開課系所︰化學系
考試日期（年月日）︰2013/01/10
考試時限（分鐘）：110
是否需發放獎勵金：是
（如未明確表示，則不予發放）
試題 :
1. Woodward has used AA to convert into Corey-like bicyclic intermediate BB
for the synthesis of a prostaglandin derivative. Desigh a useful synthetic
route for this conversion and elucidate the mechanism.
OMe OMe
＿＿︴ ＿＿︴
O ＼ O ＼
= = = =
= = = =
／＼ = ／＼ =
｜ ｜ －－－－－－→ \＿/
=＼／◣ = ◣
= = NH2 = CHO
HO = HO
OH
AA BB
Reference: J. Am. Chem. Soc., 1973, 95, 6853-6855.
Using retrosynthetic analysis, provide synthetic routes for each of the
following compounds:
Ｏ Ｏ
∥ ∥
／＼／＼
Note: EtO OEt is considered as a three-carbon starting material.
2. Ｏ
∥ Ｏ
／＼ ∥
∥ ｜ ／＼
／＼／＼ Ph
Ph Ph form
3.
COOH
Me \
＿＿▼＿＿／
＿／ ｜ ＼＿
Ｏ—＼ ｜ ／—Ｏ
Ｏ￣▲￣Ｏ
Me from starting materials with 5 carbons or less
4.
＼／
／＼
｜ ｜
//＼／\\
Ｏ Ｏ form starting materials with 5 carbons or less
5.
Ｏ
/＼ ∥
\▕／＼
□ ｜
＼／ form phenol
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