Trost, Barry M. published the artcileTotal Synthesis and Stereochemical Assignment of (-)-Ushikulide A, Safety of (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of the American Chemical Society (2009), 131(41), 15061-15074, database is CAplus and MEDLINE.
We report the determination of the full stereostructure of (-)-ushikulide A (I), a spiroketal containing macrolide by total synthesis. Ushikulide A was isolated from a culture broth of Streptomyces sp. IUK-102 and exhibits potent immunosuppressant activity (IC50 = 70 nM). To embark upon an ushikulide A synthesis, a tentative assignment was made based on analogy to cytovaricin, a related macrolide isolated from a culture of Streptomyces diastatochromogenes whose full structure was previously established via synthesis and X-ray crystallog. This report delineates studies on several key steps, namely a direct aldol reaction catalyzed by the dinuclear zinc ProPhenol complex, a metal catalyzed spiroketalization, as well as application of an unprecedented asym. alkynylation of a simple saturated aldehyde with Me propiolate to prepare the nucleophilic partner for a Marshall-Tamaru propargylation. These studies culminated in the first total synthesis and stereochem. assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies.
Journal of the American Chemical Society published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C15H21BO2, Safety of (+)-B-Methoxydiisopinocampheylborane.
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https://en.wikipedia.org/wiki/Ether,
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