54397-85-2Relevant academic research and scientific papers
Total Synthesis of Thromboxane B2via a Key Bicyclic Enal Intermediate
Aggarwal, Varinder K.,Jing, Changcheng
, (2020)
A 12-step asymmetric synthesis of thromboxane B2 (TxB2) from 2,5-dimethoxytetrahydrofuran is described. The synthesis employs our organocatalytic aldol reaction of succinaldehyde to give a key bicyclic enal intermediate. From here, the synthetic strategy involves a conjugate addition of an alkenyl side chain to the bicyclic enal, Baeyer-Villiger oxidation, and a highly Z-selective Wittig olefination of a hemiacetal. Key to success was minimizing redox operations and the manipulation of functional groups in the correct order.
Synthesis of thromboxane B2 via ketalization/ring-closing metathesis
Marvin, Christopher C.,Clemens, Alexander J. L.,Burke, Steven D.
, p. 5353 - 5356 (2008/09/17)
Total synthesis of thromboxane B2 using intermolecular ketalization followed by ring-closing metathesis is reported. Other key steps include a Sharpless asymmetric epoxidation to form an oxirane on the endo face of the bicyclic acetal, epoxide opening using lithioacetonitrile, an allylic alcohol 1,3-transposition, and Mitsunobu lactonization.
Nucleophilic polysubstituted aryl acridinium ester conjugates and syntheses thereof
-
, (2008/06/13)
This invention is directed to novel nucleophilic polysubstituted aryl acridinium conjugates and the methods for preparation thereof. The novel nucleophilic polysubstituted aryl acridinium conjugates are useful in biological assays, including novel assays for the determination of Vitamin B12, folate, cortisol, estradiol, and thromboxane B2.
Total synthesis of thromboxane B2 starting from (R,R)-tartaric acid as a chiral pool
Masaki, Yukio,Yoshizawa, Kazuhiro,Itoh, Akichika
, p. 9321 - 9324 (2007/10/03)
Optically active natural thromboxane B2 (TXB2) was synthesized from (R,R)-tartaric acid as only chiral source. The synthesis was achieved through regio- and stereoselective introduction of acetate moiety at the C2-position of the 6,8-dioxabicyclo[3.2.1]octene derivative (2) to provide an acetamide derivative (6), partial ring opening of 6 to give a pyranoid (10), and construction of the C15-hydroxyl group of TXB2 by stereospecific allylic transposition of the inherent chirality of tartaric acid in the transallylic acetate (18).
Nucleophilic polysubstituted aryl acridinium esters and uses thereof
-
, (2008/06/13)
This invention is directed to novel nucleophilic polysubstituted aryl acridinium esters and to novel conjugates thereof. The novel nucleophilic polysubstituted aryl acridinium esters and novel conjugates thereof are useful in biological assays, including novel assays for the determination of Vitamin B12, folate, cortisol, estradiol, and thromboxane B2.
Process for purification of phenylhydrazine
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, (2008/06/13)
Crude phenylhydrazine is distilled in the presence of a glycol to obtain phenylhydrazine of high purity in a high yield.
4α,6-Dihydroxy-2β-carboxaldehyde-3α-tetrahydropyranacetic acid γ-lactone, 6-alkyl ethers
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, (2008/06/13)
The present specification provides novel intermediates and novel processes for the synthesis of Thromboxane B2 (11a-homo-11a-oxa-PGF2α), its 15-epimer, and various carboxyl derivatives thereof. In particular, there are disclosed various bicyclic tetrahydropyran-containing lactones useful in the above processes, and corresponding acyclic lactones.
