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Synthesis of all diastereomers of the piperidine--alkaloid substructure of cyclopamine.

Organic letters (2009-11-04)
Philipp Heretsch, Sebastian Rabe, Athanassios Giannis
RESUMEN

All four diastereomers of the trisubstituted piperidine-alkaloids of the veratramine and jervine type were synthesized with complete stereocontrol starting from enantiopure citronellic acids. The flexible, high-yielding, and scalable route described here will facilitate convergent syntheses and give access to analogues of cyclopamine and other biologically active and diverse steroid alkaloids.

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Sigma-Aldrich
(S)-(−)-Citronellic acid, 98%
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Sigma-Aldrich
Jervine, ≥98% (HPLC), powder
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