NDLI: Total synthesis of (s)-(+)-citreofuran by ring closing alkyne metathesis.

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Total synthesis of (s)-(+)-citreofuran by ring closing alkyne metathesis.

Content Provider	Semantic Scholar
Author	Fürstner, Alois Castanet, Anne-Sophie Radkowski, Karin Lehmann, Christian W.
Copyright Year	2003
Abstract	A concise total synthesis of citreofuran 4 is described, a structurally unique octaketide derivative belonging to the curvularin family. Key steps involve the elaboration of orsellinic acid methyl ester 5 to acid 14, which converts, on attempted formation of the corresponding acid chloride, to the 3-alkoxyisocoumarin derivative 20. This heterocycle can be used as an activated ester to give ketone 21 on treatment with 3-pentynylmagnesium bromide in the presence of TMSCl as the activating agent. Ring- closing alkyne metathesis (RCAM) of diyne 21 catalyzed by (tBuO)(3)W[triple bond]CCMe(3) affords the strained cycloalkyne 22. Treatment with acid renders its triple bond susceptible to nucleophilic attack by the adjacent carbonyl group, thus leading to a transannular cycloaromatization with formation of the intact skeleton of citreofuran. An X-ray crystallographic study reveals conformational details about this natural product. Finally, it is shown that 4 as well as its protected precursor 23 are able to cleave double-stranded DNA under oxidative conditions.
File Format	PDF HTM / HTML
DOI	10.1021/jo026686q
Alternate Webpage(s)	http://pubman.mpdl.mpg.de/pubman/item/escidoc:1470055:5/component/escidoc:2173226/%5B163%5D.SI1pdf.pdf
Alternate Webpage(s)	http://pubman.mpdl.mpg.de/pubman/item/escidoc:1470055:5/component/escidoc:2173227/%5B163%5D.SI2pdf.pdf
PubMed reference number	12585897
Alternate Webpage(s)	https://doi.org/10.1021/jo026686q
Journal	Medline
Volume Number	68
Issue Number	4
Journal	The Journal of organic chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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