A new approach to the stereoselective total synthesis of isotopically labeled d-ribo-phytosphingosine

S Li, J Pang, WK Wilson, GJ Schroepfer

Index: Li, Shengrong; Pang, Jihai; Wilson, William K.; Schroepfer Jr., George J. Tetrahedron Asymmetry, 1999 , vol. 10, # 9 p. 1697 - 1707

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Citation Number: 14

Abstract

We describe a novel stereoselective total synthesis of d-ribo-[1, 1-2H-1, 2-13C] phytosphingosine (12). Chirality at the incipient C-4 position was derived from asymmetric dihydroxylation of 1-hexadecene. The remaining chiral centers were formed by Sharpless epoxidation of an allylic alcohol, followed by benzoylcarbamate cyclization to furnish a 2- amino-1, 3, 4-triol derivative with the desired stereochemistry. The 2H and 13C labels ...