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Synthesis of rac-Midpacamide and the spiro-Cyclization of Its Precursor (1997)

Lindel, Thomas ; Hoffmann, Holger

Weinheim : Wiley-Blackwell

Liebigs Annalen 1997 (1997), S. 1525-1528

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ISSN: 0947-3440

Keywords: Alkaloids ; Biomimetic synthesis ; spiro-Cyclization ; Marine sponges ; Natural products ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The alkylidene hydantoin 8 was synthesized as an analogue of the marine natural product oroidin (1) by employing a Horner-Wadsworth-Emmons reaction. Treatment of 8 with bromine in acetic acid induced a biomimetic spiro-cyclization forming the ACD ring system of dibromophakellin (2) in one step. rac-Midpacamide (10) was obtained from the same precursor through a chemoselective, ruthenium-catalyzed hydrogenation leaving the brominated pyrrole moiety intact.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199719970731

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