2 2 4 v 27 points namekey w09215e2p5 a draw a

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V. (27 points) Name:______KEy________________________ W09_215_E2_p5 A) Draw a complete step-wise curved arrow mechanism for the following transformation. Note: the mechamism takes place first under basic conditions . Please use methoxide ( - OCH 3 ) as the base. The second portion of the mechanism is under acidic conditions. You may use H-B for the acid. O O OCH 3 O O 1) NaOCH 3 , CH 3 OH OCH 3 O O O O Na + OCH 3 OCH 3 B) Complete the following reaction scheme for the conversion of starting material 1 to compound 2 by providing the necessary products. You need only show the product of the reaction of 1 (no other smaller molecular weight products need to be shown or considered in subsequent reactions.) Be sure your structure is consistent with the data provided. O HN OH O O CH 2 CH 3 O O O O O N 1) TsCl, pyridine 2) NaI C 20 H 30 INO 5 LDA compound 2 (+ enantiomer) C 20 H 29 NO 5 C 20 H 31 NO 6 THF 1 H 15 4 4 4 2) NH 4 + Cl - Provide the mechanism. Remember to add acid upon fully completing the base catalyzed portion.
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