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 | |
| Publication status | Published - 27 May 2016 |
ASJC Scopus subject areas
- Chemistry(all)
- Pharmacology, Toxicology and Pharmaceutics(all)
- Immunology
- Medicine(all)
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Manaviazar, S., Nockemann, P., & Hale, K. J. (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, 18, 2902-2905. https://doi.org/10.1021/acs.orglett.6b01235