Synthesis of Conformationally Locked Versions of Puromycin Analogues

Hisao Saneyoshi, Benoît Y. Michel, Yongseok Choi, Peter Strazewski and Victor E. Marquez
Journal of Organic Chemistry 2008, 73, 9435-9438

Synthesis of Conformationally Locked Versions of Puromycin Analogues

Conformationally locked North and South versions of puromycin analogues built on a bicyclo[3.1.0]hexane pseudosugar template were synthesized. The final assembly of the products was accomplished by the Staudinger-Vilarrasa coupling of the corresponding North (2 and 3) and South (6 and 7) 3'-azidopurine carbanucleosides with the Fmoc-protected 1-hydroxybenzotriazole ester of 4-methoxy-L-tyrosine. North azides 2 and 3 were reported earlier. The 3'-azido intermediates 6 and 7 that are required for the synthesis of the South puromycin analogues are described herein for the first time.