Cryptopleurine and Julandine

Reagents i. BusLi, TMEDA, THF, Et20, at —78 °C. then 2-formylpyridine ii, TsOH, PhMe, heat iii, Zn-Cu, 10% KOH. pyridine iv. H2, Pt. AcOH. HC1. then heat with xylene v. LiAlH4, THF 

Silicon (iv) chloride is an effective Lewis acid in the cyclization and subsequent dehydration steps of Herbert s synthesis of julandine and of cryptopleurine (cf. Vol. 10, p. 72).27 An early cryptopleurine synthesis has been improved.28 

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Sydnes MO, Bezos A, Bums C, Kruszelnicki I, Parish CR, Su S, Rae AD, Willis AC, Banwell MG (2008) Synthesis and biological evaluation of some enantiomerically pure C8c-C15 monoseco analogues of the phenanthroquinolizidine-type alkaloids cryptopleurine and julandine. Aust J Chem 61(7) 506-520. doi 10.1071/ch08190... 

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