Total synthesis of DL-prostaglandin E1

N Finch, L DellaVecchia, JJ Fitt…

Index: Finch,N. et al. Journal of Organic Chemistry, 1973 , vol. 38, # 26 p. 4412 - 4424

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Citation Number: 27

Abstract

dl-Prostaglandin E1 (PGE1 j (61) has been synthesized in 14 steps from 2-carboxy-5-oxo-1- cyclopenteneheptanoic acid (15). The synthesis required the development of two mild procedures and a new protecting group. A Moffatt oxidation using a water-soluble carbodiimide converted the carbinol 52 to aldehyde 53. The Wittig reaction of aldehyde 53 with the tributylphosphorane 36 was used to obtain the enone 54. Protection of the ...