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

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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 languageEnglish
Pages (from-to)2902-2905
Number of pages4
JournalOrganic Letters
Volume18
DOIs
Publication statusPublished - 27 May 2016

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Stereochemistry
Macrolides
stereochemistry
Immunosuppressive Agents
amines
fragments
nuclear magnetic resonance
synthesis
Amines
Nuclear magnetic resonance
JBIR-04
SW-163A
prunustatin A

Cite this

Manaviazar, Soraya ; Nockemann, Peter ; Hale, Karl J. / 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. In: Organic Letters. 2016 ; Vol. 18. pp. 2902-2905.
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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 = "5",
day = "27",
doi = "10.1021/acs.orglett.6b01235",
language = "English",
volume = "18",
pages = "2902--2905",
journal = "Organic Letters",
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Manaviazar, S, Nockemann, P & Hale, KJ 2016, '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', Organic Letters, vol. 18, pp. 2902-2905. https://doi.org/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. / Manaviazar, Soraya; Nockemann, Peter; Hale, Karl J.

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

Research output: Contribution to journal › Article

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 -

Manaviazar S, Nockemann P, Hale KJ. 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. Organic Letters. 2016 May 27;18:2902-2905. https://doi.org/10.1021/acs.orglett.6b01235

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