Tetrahedron Letters

Total synthesis of (−)-centrolobine

T Takeuchi, M Matsuhashi, T Nakata

Index: Takeuchi, Toshiharu; Matsuhashi, Miyuki; Nakata, Tadashi Tetrahedron Letters, 2008 , vol. 49, # 45 p. 6462 - 6465

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Citation Number: 30

Abstract

We have recently reported that treatment of an acyclic iodo-ester with n- or t-butyllithium effected intramolecular cyclization to give the hemiacetal, which was reduced with Et 3 SiH in the presence of BF 3 ·Et 2 O to give 2,6-syn-tetrahydropyran. 7 As an application of this method to the synthesis of natural products, we focused our attention on the synthesis of (−)-centrolobine (1). Retrosynthetic analysis revealed two possible synthetic routes, A and B, using iodo-esters 2 and 3, ...