Carneiro, Vania M. T. published the artcileCoibacins A and B: Total Synthesis and Stereochemical Revision, Quality Control of 57044-25-4, the publication is Journal of Organic Chemistry (2014), 79(2), 630-642, database is CAplus and MEDLINE.
The interface between synthetic organic chem. and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Therefore, the correct structure is I. Addnl., we synthesized the corrected structure for coibacin B, II, on the basis of the assignment of configuration for coibacin A.
Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Quality Control of 57044-25-4.
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