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Total synthesis of ?¹²-prostaglandin J?, a highly potent and selective antileukemic agent.

ABSTRACT: A catalytic asymmetric total synthesis of the potent and selective antileukemic ?(12)-prostaglandin?J3 (?(12)-PGJ3) is described. The convergent synthesis proceeded through intermediates 2 and 3, formed enantioselectively from readily available starting materials and coupled through an aldol reaction followed by dehydration to afford stereoselectively the cyclopentenone alkylidene structural motif of the molecule.

SUBMITTER: Nicolaou KC

PROVIDER: S-EPMC4169176 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Total synthesis of Δ¹²-prostaglandin J₃, a highly potent and selective antileukemic agent.

Nicolaou K C KC Heretsch Philipp P ElMarrouni Abdelatif A Hale Christopher R H CR Pulukuri Kiran K KK Kudva Avinash K AK Narayan Vivek V Prabhu K Sandeep KS

Angewandte Chemie (International ed. in English) 20140805 39

A catalytic asymmetric total synthesis of the potent and selective antileukemic Δ(12)-prostaglandin J3 (Δ(12)-PGJ3) is described. The convergent synthesis proceeded through intermediates 2 and 3, formed enantioselectively from readily available starting materials and coupled through an aldol reaction followed by dehydration to afford stereoselectively the cyclopentenone alkylidene structural motif of the molecule. ...[more]

PMID: 25098181

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