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 |
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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)