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Explain the stereoselectivity observed in step h? • What other ester could have directly afforded compound 7 via a Claisen rearrangement? • Suggest a mechanism for the formation of compound 8, obtained upon ozonolysis of vinylsilane 7. 22 16. Stereoselective Total Synthesis of (+)-Artemisinin Further Reading • For an analysis of recent syntheses of artemisinin, see: M. G. Constantino, M. Beltrame and G. V. J. Dasilva, Synth. -S. -X. Xu, Acc. Chem. , 1994,27, 211216. • For syntheses of structural analogues of artemisinin, see: G.

Raimondi, Gazz. Chim. , 1989, 779, 253. • For reviews of the Mitsunobu reaction, see: D. L. Hughes, Org. React, 1992,42, 335; D. L. , 1996,28, 127. 39 28. Total Synthesis of the Enantiomer of Hennoxazole A P. Wipf and S. Lira, J. Am. Chem. , 1995, 777, 558. Abstracted with permission from J. Am. Chem. , 1995,117, 558 ©1995 American Chemical Society Discussion Points • What is the mechanism of the Evans-Mislow rearrangement in step c? • Suggest a mechanism for the formation of compound 5. • Explain the stereoselectivity observed in the Luche reduction step j.

For a review on enantioselective reduction of ketones, see: V. K. Singh, Synthesis, 1992, 7, 607. For a review on the diastereoselectivity in nucleophilic additions to unsymmetrically substituted carbonyls, see: B. W. Gung, Tetrahedron, 1996, 52, 5263. For reviews on the synthesis of chiral epoxides, see: P. Besse and H. Veschambre, Tetrahedron, 1994,50, 8885; W. Adam and M. J. Richter, Ace. Chem. , 1994, 27, 57; K. A. J0rgensen, Chem. , 1989, 59,431. For a review on substrate-directable reactions, see: A.

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