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Oxidative fragmentation of 5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate

Oksidativne fragmentacije 5-hidroksi-1-okso-5α-holestan-3β-il-acetata

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2003
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Authors
Krstić, Natalija
Bjelaković, Mira
Lorenc, Ljubinka
Pavlović, Vladimir D.
Article (Published version)
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Abstract
5-hydroxy-1-oxo-5α-cholestan-3β-yl acetate (11) was prepared in 5 steps starting from (E)-3β-acetoxy-5,10-seco-1(10)-cholesten-5-one (6). Treatment of the 1-oxo-5-hydroxy derivative 11 with lead tetraacetate (LTA) (under thermal or hypoiodite conditions) or with mercuric oxide/iodine (HgO/I2) reagent resulted in the oxidative β-fragmentation of the C(5)–C(10) bond affording 1,5-dioxo-5,10-secocholest-10(19)-en-3β-yl acetate (12), in different yields, depending on the reagent. Also the stereochemistry of the 1β,6β-cyclization product 13, formed by transannular cyclization of the 1,5-diketone 12 on silica gel, is discussed in this work.
Sintetizovan je 5-hidroksi-1-okso-5α-holestan-3β-il-acetata (11) u 5 faza polazeći od (E)- 3β-acetoksi-5,10-seko-1(10)-holesten-5-ona (6). Dejstvom olovo-tetraacetata (LTA) (pod termičkim ili hipojoditnim uslovima), ili merkuri-oksid/jodnog reagensa (HgO/I2) na 1-okso-5-hidroksi derivat 11, vrši se oksidativna β-fragmentacija njegove C(5)–C(10) veze, pri čemu se dobija 1,5-diokso-5,10-sekoholest-10(19)-en-3β-il-acetat (12), u različitim prinosima u zavisnosti od upotrebljenog reagensa. Takođe, diskutovana je stereohemija 1β,6β-ciklizacionog proizvoda 13, nastalog intramolekulskom ciklizacijom 1,5-diokso-5,10-seko jedinjenja 12 na silika gelu.
Keywords:
5-Hydroxy-1-oxo-5α-cholestan-3β-yl acetate / 1,5-dioxo-5,10-secocholest-10(19)-en-3β-yl acetate / β-fragmentation / transannular cyclization
Source:
Journal of the Serbian Chemical Society, 2003, 68, 11, 785-794
Publisher:
  • Serbian Chemical Society
Projects:
  • Project MESTD, br. 1702: Synthesis and chemical transformations of steroidal and modified steroidal molecules

DOI: 10.2298/JSC0311785K

ISSN: 0352-5139

WoS: 000187394400001

Scopus: 2-s2.0-1442310833
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/109
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