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

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

doi:10.1002/anie.201404917

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

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

Research output: Contribution to journal › Article › peer-review

40 Scopus citations

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.

Original language	English (US)
Pages (from-to)	10443-10447
Number of pages	5
Journal	Angewandte Chemie (International ed. in English)
Volume	53
Issue number	39
DOIs	https://doi.org/10.1002/anie.201404917
State	Published - Sep 22 2014

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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10.1002/anie.201404917

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title = "Total synthesis of Δ¹²-prostaglandin J₃, a highly potent and selective antileukemic agent",

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.",

author = "Nicolaou, \{K. C.\} and Philipp Heretsch and Abdelatif ElMarrouni and Hale, \{Christopher R.H.\} and Pulukuri, \{Kiran K.\} and Kudva, \{Avinash K.\} and Vivek Narayan and Prabhu, \{K. Sandeep\}",

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year = "2014",

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doi = "10.1002/anie.201404917",

language = "English (US)",

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T1 - Total synthesis of Δ¹²-prostaglandin J₃, a highly potent and selective antileukemic agent

AU - Nicolaou, K. C.

AU - Heretsch, Philipp

AU - ElMarrouni, Abdelatif

AU - Hale, Christopher R.H.

AU - Pulukuri, Kiran K.

AU - Kudva, Avinash K.

AU - Narayan, Vivek

AU - Prabhu, K. Sandeep

PY - 2014/9/22

Y1 - 2014/9/22

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84964315095

UR - https://www.scopus.com/pages/publications/84964315095#tab=citedBy

U2 - 10.1002/anie.201404917

DO - 10.1002/anie.201404917

M3 - Article

C2 - 25098181

AN - SCOPUS:84964315095

SN - 1433-7851

VL - 53

SP - 10443

EP - 10447

JO - Angewandte Chemie (International ed. in English)

JF - Angewandte Chemie (International ed. in English)

IS - 39

ER -

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

Abstract

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