Anomalous Chromophore Disruption Enables an Eight-Step Synthesis and Stereochemical Reassignment of (+)-Marineosin A.

Autor:	Feng Z; Department of Chemistry and Biochemistry , University of California-Los Angeles , 607 Charles E. Young Drive East , Los Angeles , California 90095-1569 , United States., Allred TK; Department of Chemistry and Biochemistry , University of California-Los Angeles , 607 Charles E. Young Drive East , Los Angeles , California 90095-1569 , United States., Hurlow EE; Department of Chemistry and Biochemistry , University of California-Los Angeles , 607 Charles E. Young Drive East , Los Angeles , California 90095-1569 , United States., Harran PG; Department of Chemistry and Biochemistry , University of California-Los Angeles , 607 Charles E. Young Drive East , Los Angeles , California 90095-1569 , United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2019 Feb 13; Vol. 141 (6), pp. 2274-2278. Date of Electronic Publication: 2019 Jan 31.
DOI:	10.1021/jacs.9b00396
Abstrakt:	An eight-step asymmetric synthesis of (+)-marineosin A is described. The route proceeds by condensing fragments of reversed polarity relative to conventional prodiginine constructions. The resultant unstable chromophore is disrupted by a unique cycloisomerization promoted at a tailored manganese surface. This provides a premarineosin and subsequently marineosin A in a particularly concise manner. A pyridinophane N-oxide photorearrangement in flow and structural isomers of premarineosin are discussed, as is the reassignment of marineosin stereochemistry. The route gives access to the natural product as well as diastereomers, congeners and analogs that are currently inaccessible by other means.
Databáze:	MEDLINE
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