Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR- 04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A

Soraya Manaviazar; Peter Nockemann; Karl J Hale

doi:10.1021/acs.orglett.6b01235

Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR- 04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A

Soraya Manaviazar, Peter Nockemann, Karl J Hale

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

10 Citations (Scopus)

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Abstract

A unified total synthesis of the GRP78-downregulator(+)-prunustatin A and the immunosuppressant(+)-SW-163A based upon [1 + 1 + 1 + 1]-fragment condensationand macrolactonization between O(4) and C(5) is hereindescribed. Sharpless asymmetric dihydroxylation was used toset the C(2) stereocenter present in both targets. In like fashion,coupling of the (+)-prunustatin A macrolide amine with benzoicacid furnished a JBIR-04 diastereoisomer whose NMR spectradid not match those of JBIR-04, thus confirming that it hasdifferent stereochemistry than (+)-prunustatin A.

Original language	English
Pages (from-to)	2902-2905
Number of pages	4
Journal	Organic Letters
Volume	18
DOIs	https://doi.org/10.1021/acs.orglett.6b01235
Publication status	Published - 27 May 2016

ASJC Scopus subject areas

Chemistry(all)
Pharmacology, Toxicology and Pharmaceutics(all)
Immunology
Medicine(all)

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Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR- 04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A
© 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
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Karl Hale
- k.j.hale@qub.ac.uk
- School of Chemistry and Chemical Engineering - Professor
- Organic Synthesis and Chemical Biology
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title = "Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR- 04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A",

abstract = "A unified total synthesis of the GRP78-downregulator(+)-prunustatin A and the immunosuppressant(+)-SW-163A based upon [1 + 1 + 1 + 1]-fragment condensationand macrolactonization between O(4) and C(5) is hereindescribed. Sharpless asymmetric dihydroxylation was used toset the C(2) stereocenter present in both targets. In like fashion,coupling of the (+)-prunustatin A macrolide amine with benzoicacid furnished a JBIR-04 diastereoisomer whose NMR spectradid not match those of JBIR-04, thus confirming that it hasdifferent stereochemistry than (+)-prunustatin A.",

author = "Soraya Manaviazar and Peter Nockemann and Hale, {Karl J}",

year = "2016",

month = may,

day = "27",

doi = "10.1021/acs.orglett.6b01235",

language = "English",

volume = "18",

pages = "2902--2905",

journal = "Organic Letters",

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}

Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR- 04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A. / Manaviazar, Soraya ; Nockemann, Peter ; Hale, Karl J.

In: Organic Letters, Vol. 18, 27.05.2016, p. 2902-2905.

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

TY - JOUR

T1 - Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR- 04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A

AU - Manaviazar, Soraya

AU - Nockemann, Peter

AU - Hale, Karl J

PY - 2016/5/27

Y1 - 2016/5/27

N2 - A unified total synthesis of the GRP78-downregulator(+)-prunustatin A and the immunosuppressant(+)-SW-163A based upon [1 + 1 + 1 + 1]-fragment condensationand macrolactonization between O(4) and C(5) is hereindescribed. Sharpless asymmetric dihydroxylation was used toset the C(2) stereocenter present in both targets. In like fashion,coupling of the (+)-prunustatin A macrolide amine with benzoicacid furnished a JBIR-04 diastereoisomer whose NMR spectradid not match those of JBIR-04, thus confirming that it hasdifferent stereochemistry than (+)-prunustatin A.

AB - A unified total synthesis of the GRP78-downregulator(+)-prunustatin A and the immunosuppressant(+)-SW-163A based upon [1 + 1 + 1 + 1]-fragment condensationand macrolactonization between O(4) and C(5) is hereindescribed. Sharpless asymmetric dihydroxylation was used toset the C(2) stereocenter present in both targets. In like fashion,coupling of the (+)-prunustatin A macrolide amine with benzoicacid furnished a JBIR-04 diastereoisomer whose NMR spectradid not match those of JBIR-04, thus confirming that it hasdifferent stereochemistry than (+)-prunustatin A.

U2 - 10.1021/acs.orglett.6b01235

DO - 10.1021/acs.orglett.6b01235

M3 - Article

VL - 18

SP - 2902

EP - 2905

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

ER -

Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR- 04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A

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