808771-39-3

Upstream product

• 4039-83-2 3-(4-methoxybenzyloxy)propyne 
• 124150-87-4 tert-butyldimethylsilyl (R)-glycidyl ether 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 11076-19-0 bongkrekic acid 
• 1174549-31-5 (R,Z)-2-methoxy-6-((4-methoxyphenyl)methoxy)hex-4-en-1-ol 
• 847909-75-5 C₁₅H₂₀O₄ 
• 847909-76-6 (5R)-1-(7,7-dibromo-5-methoxyhepta-2,6-dienyloxymethyl)-4-methoxybenzene 
• 1174549-32-6 (R,Z)-ethyl 4-methoxy-8-((4-methoxyphenyl)methoxy)oct-6-en-2-ynoate 
• 1174549-42-8 (4R)-ethyl 4-methoxy-8-(4-methoxybenzyloxy)-3-methylocta-2,6-dienoate 
• 1174549-43-9 (R,2Z,6Z)-4-methoxy-8-(4-methoxyphenyl)methoxy-3-methylocta-2,6-dien-1-ol 

Relevant academic research and scientific papers

Efficient Total Synthesis of Bongkrekic Acid and Apoptosis Inhibitory Activity of Its Analogues

Bongkrekic acid (BKA), isolated from the bacterium Burkholderia cocovenenans, is an inhibitor of adenine nucleotide translocator, which inhibits apoptosis, and is thus an important tool for the mechanistic investigation of apoptosis. An efficient total synthesis of BKA has been achieved by employing a three-component convergent strategy based on Kocienski-Julia olefination and Suzuki-Miyaura coupling. It is noteworthy that segment B has been prepared as a new doubly functionalized coupling partner, which contributes to shortening of the number of steps. Torquoselective olefination with an ynolate has also been applied for the efficient construction of an unsaturated ester. Furthermore, it is revealed that 1-methyl-2-azaadamantane N-oxyl is an excellent reagent for final oxidation to afford BKA in high yield. Based on the total synthesis, several BKA analogues were prepared for structure-activity relationship studies, which indicated that the carboxylic acid moieties were essential for the apoptosis inhibitory activity of BKA. More easily available BKA analogues with potent apoptosis inhibitory activity were also developed. Stripped BKA: The highly efficient second-generation total synthesis of bongkrekic acid (BKA), an apoptosis inhibitor, has been developed. The synthesis features a three-component convergent strategy based on a Kocienski-Julia olefination and Suzuki-Miyaura coupling. The structure-activity relationship (SAR) is also examined for the first time (see scheme).

Efficient synthesis of bongkrekic acid. Three-component convergent strategy

An efficient total synthesis of the apoptosis inhibitor bongkrekic acid was accomplished using a three-component convergent strategy involving a Kocienski-Julia olefination and a Suzuki-Miyaura coupling, in which the longest linear sequence was 18 steps and proceeded in 6.4% overall yield. The torquoselective olefination also contributed to the shortening of the synthesis.

Total synthesis of (+)-bongkrekic acid

Total synthesis of bongkrekic acid, an important apoptosis inhibitor, has been accomplished. The strategy includes inexpensive starting materials, asymmetric alkylation, anionic allyl coupling and oxidative manipulations. This process would provide a sufficient amount of bongkrekic acid and its analogues.