220271-25-0

Upstream product

• 130874-90-7 4,5-dimethyl (4R,5R)-2-(4-methoxyphenyl)-1,3-dioxolane-4,5-dicarboxylate 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 156768-68-2 (2S,3S)-2,3-O-(4-methoxybenzylidene)-1,2,3,4-butanetetraol 

Downstream Products

• 1361254-14-9 (4S,5S)-2-(4-methoxyphenyl)-4,5-bis(propa-1,2-dienyl)-1,3-dioxolane 
• 1361254-27-4 (4S,5S)-5-(4-methoxybenzyloxy)octa-1,2,6,7-tetraen-4-ol 
• 1361254-13-8 (4S,5S)-4-(4-methoxybenzyloxy)-5-methoxymethoxy-1,2,6,7-octatetraene 
• 1361254-33-2 (3S,4S)-4-(4-methoxybenzyloxy)hexa-1,5-diyn-3-ol 
• 1361253-98-6 (1E,5E)-1-(4-methoxybenzyloxy)-6-methoxymethoxy-3,4-dimethylenehexa-1,5-diene 

Relevant academic research and scientific papers

Concise synthesis of the bicyclic core of the chromoprotein antibiotics kedarcidin and neocarzinostatin by transannular reductive cyclization of a tetrayne precursor

The oxygenated [7.3.0]-bicyclododecadienediyne 8 is synthesized in 9 steps from L,-dimethyl tartrate. In the key transformation, transannular reductive cyclizalion of the potassium salt of the tetrayne alcohol 7 with NaAIH(OCH2CH2(NCH3)2) affords the bicyclic product 8 in 50-54% yield. This sequence provides a rapid entry into the strained bicyclic core structures of kedarcidin and neocarzinostatin chromophores (1 and 2, respectively).

Cu-Promoted [2 + 2] cycloaddition of 1,4-bisallenes

The thermal reaction of 1,4-bisallenes with the aid of Cu salt/amine significantly suppressed the formal [3,3] sigmatropic rearrangement resulting in the highly selective formation of the bicyclo[4.2.0]octadiene framework. This reaction could be applied to the one-pot synthesis of bicyclo[4.2.0]octadienes from 1,5-hexadiynes via the Crabbe homologation.