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Unformatted text preview: N H CO 2 Me O MeO 2 C H N MeO 2 C Me O H 1. NaBH 4 2. Ms 2 O 3. LiBr Ms 2 O = S O S O O O O Me Me N H CO 2 Me O MeO 2 C H N MeO 2 C Me Br Problem 5 Many tumors in breast cancer are estrogen-dependent. Drugs that interfere with estrogen binding have antitumor activity and may even help prevent tumor occurrence. A widely used antiestrogen drug is tamoxifen. Given that tamoxifen is synthesized from A using an enamine intermediate synthesized from A and a Grignard reagent, propose a synthesis of tamoxifen. O O N O N tamoxifen A Problem 6 The Wolff-Kishner reaction and the Wharton fragmentation use hydrazine (H 2 NNH 2 ) to make a hydrazone and involve the loss of N 2 . Propose a mechanism for the following Wharton fragmentation reaction. O O OH 1. H 2 NNH 2 , Heat 2. Acidic Workup + N 2...
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- Spring '09