36969-85-4Relevant academic research and scientific papers
Applications of 5-Endo-trigonal cyclization: Construction of compounds relevant to the synthesis of prostaglandins and methyl epi-Jasmonate
Sannigrahi, Mousumi,Mayhew, Darrin L.,Clive, Derrick L. J.
, p. 2776 - 2788 (2007/10/03)
Silane 15, easily constructed by simple methods, undergoes a cascade of radical reactions when treated with a stannane to afford the bicyclic 1,2-oxasiloles 16, with the major isomer having the ester group anti to the O-Si unit. This isomer was elaborated via 19 into 6, a deoxy derivative of the Corey lactone. In a related sequence, ketone 24 was converted into silane 35; this, too, underwent the radical cascade to afford the highly substituted 1,2-oxasiloles 36. Again the major isomer had the ester and O-Si units in an anti relationship. Elaboration of 36 (major isomer) gave the Corey lactone derivative 7. A key intermediate (32) in this second sequence was also prepared in optically pure form by starting with 2-deoxy-D-ribose. Compound 19 was converted into 8, a sequence that constitutes a formal synthesis of methyl (±)-epi-jasmonate. Two examples were found of selective silylation of a propargylic secondary hydroxyl in the presence of an ordinary secondary hydroxyl.
SYNTHESIS OF 11-COREY'S 11-DEOXYALDEHYDE - A PROSTAGLANDIN SYNTHON - FROM 1,5-CYCLOOCTADIENE
Dyadchenko, M. A.,Danilova, G. A.,Spanig, I.,Schick, G.,Pivnitskii, K. K.
, p. 2198 - 2202 (2007/10/02)
A new scheme was developed for the synthesis of 6-formyl-cis-2-oxabicyclooctan-3-ones epimeric with respect to the aldehyde group, which are prostaglandin synthons and 11-deoxy analogs of Corey's aldehyde previously used in prostanoid synthesis.The starting material was 1,5-cyclooctadiene, which gives the synthons with an overall yield of up to 24percent in five or eight stages in the two versions of the scheme.
PROSTANOIDS. VII. trans-2,3-DIETHOXYCARBONYLCYCLOPENTANONE IN THE SYNTHESIS OF PROSTAGLANDINS
Tolstikov, G. A.,Miftakhov, M. S.,Akbutina, F. A.
, p. 268 - 277 (2007/10/02)
2,3-Diethoxycarbonylcyclopentanone was synthesized from methyl 3-cyclohexenecarboxylate; its telomerization with 1,3-butadiene gave 2-(2,7-octadienyl)2,3-diethoxycarbonylcyclopentanone, which was then transformed into 2α-(2,7-octadienyl)-3β-(3α-hydroxy-1-trans-octenyl)-1α-cyclopentanol, i.e., an analog of 11-deoxyprostaglandin-F1α.The key synthon for the synthesis of 11-deoxy-α-homoprostaglandin-E1 was obtained from 2-(2,7-octadienyl)-3-ethoxycarbonylcyclopentanone.A new method was developed for the production of the γ-lactone of 5α-hydroxy-2β-(3-oxo-1-trans-octenyl)-1α-cyclopentaneacetic acid - a well-known synthon in the synthesis of 11-deoxyprostaglandin-E2.The method was based on the alkylation of 2,3-diethoxycarbonylcyclopentanone with allyl bromide.
