By Carey F., Sundberg R.
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Extra resources for Advanced Organic Chemistry. Structure and Mechanisms
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.
M. Wovkulich, K. Shankaran, J. Kigiel and M. R. Uskokovic, J. Org. , 1993,55, 832. 36 26. Total Synthesis of 1233 A Discussion Points • What is the mechanism of the Noyori catalyst-mediated asymmetric hydrogenation step a? • Explain the diastereoselectivity observed in the [2,3]-rearrangement of step i. • During the hydroboration step, a substantial amount of compound 13 was formed. Suggest a way to convert it into the desired epimer 8 by exploiting the latent symmetry of the system. ,OTBDMS OH OH Further Reading • For the influence of trace amount of acid in the ruthenium (II)-BINAP catalysed asymmetric hydrogenation, see: S.
1994,35, 2091. , 1994,3S, 2091 ©1994 Elsevier Science Ltd 44 31. Studies Towards the Total Synthesis of Rapamycin Discussion Points • How would it be possible to recycle the undesired syn isomer obtained in step a? • What is the mechanism of step c? • Explain the diastereoselectivity observed in the (E)-crotylborane addition to aldehyde 4. • Rationalise the diastereoselectivity observed in the epoxidation of homoallylic alcohol 5. How could the stereoselectivity of this reaction be reversed? Further Reading • For an analysis of the mechanism in the oxazaborolidine catalysed reduction of ketones, see: B.
Advanced Organic Chemistry. Structure and Mechanisms by Carey F., Sundberg R.