A simple procedure for the synthesis of γ-hydroxy-α,β-(E)-alkenoic esters: formal synthesis of (+)-macrosphelides A and B

Srinivasa Rao, K. ; Mukkanti, K. ; Srinivasa Reddy, D. ; Pal, Manojit ; Iqbal, Javed (2005) A simple procedure for the synthesis of γ-hydroxy-α,β-(E)-alkenoic esters: formal synthesis of (+)-macrosphelides A and B Tetrahedron Letters, 46 (13). pp. 2287-2290. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/j.tetlet.2005.02.004

Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.02.004

Abstract

A highly trans-selective conjugate reduction of γ-hydroxy-α,β-alkynoic esters to produce γ-hydroxy-α,β-(E)-alkenoic esters using LiAlH4 is reported. The application of this methodology is demonstrated by a formal synthesis of the potent cell–cell adhesion inhibitors (+)-macrosphelides A and B.

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