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Synthesis of New unnatural Macrocyclic Trichothecenes: 4-epiverrucarin A. 47th Communication on verrucarins and roridins46th Commun.: [1]. (1988)

Jeker, Nicolas ; Tamm, Christoph

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 71 (1988), S. 1904-1913

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The 4-epiverrucarin A (24), a new unnatural macrocyclic trichothecene, was synthesized starting from 4-epiverrucarol (20). The latter was obtained by metal-hydride reduction of the 4-oxo derivative 19. Subsequent conversion of 20 into the monoester 30 and then the diester 32 followed by macrolactonization of the latter yielded 4-epiverrucarin A (24). Attempts to invert the configuration of the naturally occuring 3α-OH group of a trichothecene were unsuccessful. The cytostatic (P-815) and immunosuppressive (MLR) activity of several natural and unnatural trichothecenes was determined in vitro.

Additional Material: 3 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19880710809

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