Literature DB >> 25098181

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

K C Nicolaou1, Philipp Heretsch, Abdelatif ElMarrouni, Christopher R H Hale, Kiran K Pulukuri, Avinash K Kudva, Vivek Narayan, K Sandeep Prabhu.   

Abstract

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.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; asymmetric catalysis; leukemia; natural products; total synthesis

Mesh：

Substances：

Year:  2014        PMID： 25098181      PMCID： PMC4169176          DOI： 10.1002/anie.201404917

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  12 in total

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Authors:  Joshua D Brooks; Ginger L Milne; Huiyong Yin; Stephanie C Sanchez; Ned A Porter; Jason D Morrow
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9.  Evaluation of the stability, bioavailability, and hypersensitivity of the omega-3 derived anti-leukemic prostaglandin: Δ(12)-prostaglandin J3.

Authors:  Avinash K Kudva; Naveen Kaushal; Sonia Mohinta; Mary J Kennett; Avery August; Robert F Paulson; K Sandeep Prabhu
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5.  Reoptimization of the Organocatalyzed Double Aldol Domino Process to a Key Enal Intermediate and Its Application to the Total Synthesis of Δ12 -Prostaglandin J3.

Authors:  Andrejs Pelšs; Narasimhulu Gandhamsetty; James R Smith; Damien Mailhol; Mattia Silvi; Andrew J A Watson; Isabel Perez-Powell; Sébastien Prévost; Nina Schützenmeister; Peter R Moore; Varinder K Aggarwal
Journal:  Chemistry       Date:  2018-06-06       Impact factor: 5.236
  5 in total

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