202846-63-7

Upstream product

• 97-67-6 (S)-Malic acid 
• 54555-84-9 benzyl iodoethyl ether 
• 73840-71-8 diethyl (2S,3R)-(+)-2-hydroxy-3-methylsuccinate 
• 344357-29-5 (2S,3R)-5-benzyloxy-3-ethoxycarbonyl-2-hydroxy-3-methylpentanoic acid 
• 202846-62-6 (2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester 

Downstream Products

• 344357-30-8 (3S,4S)-4-(2-benzyloxyethyl)-3-methoxymethyloxy-4-methyl-γ-butyrolactone 
• 947596-42-1 C₁₄H₁₆O₄ 
• 165170-94-5 (5S,9S)-9-methyl-2-phenyl-9-vinyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione 
• 344357-31-9 (3S,4S)-3-methoxymethyloxy-4-methyl-4-[2-(2-nitrophenyl)seleno]-γ-butyrolactone 
• 344357-19-3 (S)-3-[1-Hydroxy-2-(2-phenyl-[1,3]dioxolan-2-yl)-ethyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one 
• 344357-25-1 (3R,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone 
• 344357-20-6 (3S,4R)-3-[3',3'-(ethylenedioxy)-3'-phenylpropanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone 
• 344357-32-0 (S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one 
• 344357-26-2 (3R,4R,3'R,4'S)-3-[3'-(4-methoxybenzyloxy)-4'-methylhexanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone 
• 344357-21-7 (3S,4R,3'R,4'S)-3-[3'-(4-methoxybenzyloxy)-4'-methylhexanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone 

Relevant academic research and scientific papers

Total synthesis and revised structure of biyouyanagin A

(Chemical Equation Presented) It all adds up: A 12-step total synthesis of biyouyanagin A, an inhibitor of HIV replication, has revealed its structure, rendered it available for biological investigations, and allows the synthesis of analogues. The convergent synthesis involves two cascade sequences and a remarkably selective [2+2] cycloaddition reaction to forge the cyclobutane ring of the target molecule in the ultimate step.

Synthesis of Hyperolactones A and C

Hyperolactones A (1) and C (3) have been synthesized starting from (S)-malic acid by a straightforward route. The unique spirolactone skeleton was efficiently constructed by one-pot reaction as a key step. The absolute stereochemistry of hyperolactones was unambiguously established by this synthesis.

Synthesis and absolute configuration of (+)-hyperolactone B

The synthesis of (+)-hyperolactone B 2, isolated from Hypericum chinense L., was accomplished from (S)-malic acid. The synthesis unambiguously established the absolute stereochemistry of hyperolactone B.