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Beilstein J. Org. Chem. 2013, 9, 2358–2366, doi:10.3762/bjoc.9.271
Graphical Abstract
Figure 1: Structures of some pumiliotoxins and an advanced intermediate.
Scheme 1: Synthesis of 5 from 6 via oxidation–addition sequence.
Scheme 2: Plausible stereochemical course of the preferential axial addition of methylmagnesium iodide to bic...
Scheme 3: Holmes’ exclusive trans-diastereoselective methylation of N-Cbz-protected piperidin-3-one 8.
Scheme 4: Our plan for the trans-diastereoselective methylation of keto-lactam 10.
Scheme 5: Retrosynthetic analysis of (8S,8aS)-8-hydroxy-8-methylindolizidin-5-one (5).
Scheme 6: Synthesis of compound 18.
Scheme 7: Synthesis of hydroxylactam 18.
Scheme 8: Synthesis of tertiary alcohol 22.
Scheme 9: Synthesis of (8S,8aS)-5 and its silyl ether 23.