Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 22, Pages 7552-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9024929
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- NIH [CA1225601, AI 038897]
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Muironolide A, a new chemical entity with an unprecedented chlorinated hexahydro-1H-isoindolone skeleton, was isolated in only 90 mu g yield from the same marine sponge, Phorbas sp. that also provided phorboxazoles A and B. The structure was solved by interpretation of NMR data obtained at 600 MHz with a 1.7 mm cryo-microprobe in combination with FTMS, exciton coupled CD, and stereochemical. correlation with authentic standards prepared by Reformatsky reaction of (-)-(1R,2S)-2-chloro-1-cyclopropanecarboxaldehyde. The absolute configuration of the chlorocyclopropane ring in 1 is opposite to that of co-occurring phorbasides A-F. Muironolide A is the first described macrolide bearing an esterified trichloromethyl carbinol, and may be produced by a cyanobacterium that also makes phorbasides.
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