165170-94-5

Upstream product

• 27773-03-1 ethyl 3,3-(ethylenedioxy)-3-phenylpropanoate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 344357-31-9 (3S,4S)-3-methoxymethyloxy-4-methyl-4-[2-(2-nitrophenyl)seleno]-γ-butyrolactone 
• 1046160-25-1 C₂₂H₁₉NO₆Se 
• 73627-97-1 (R)-3-phenyl-3-hydroxypropanenitrile 
• 20780-54-5 (S)-styrene oxide 
• 56318-28-6 (bis(allyloxy)methyl)benzene 
• 1334180-32-3 (4R)-N-[(3R)-3-allyloxy-3-phenylpropanoyl]-4-phenyl-1,3-thiazolidine-2-thione 
• 1334180-38-9 ethyl (R)-2-diazo-5-[(2E)-3-methyl-4-(trimethylsilyloxy)but-2-enyloxy]-3-oxo-5-phenylpentanoate 
• 1334180-37-8 ethyl (R)-2-diazo-5-[(2E)-3-methyl-4-hydroxybut-2-enyloxy]-3-oxo-5-phenylpentanoate 
• 1334180-24-3 ethyl (R)-2-diazo-5-[(2E)-3-methyl-4-oxobut-2-enyloxy]-3-oxo-5-phenylpentanoate 
• 1334180-36-7 ethyl (R)-2-diazo-3-oxo-5-(2-oxoethoxy)-5-phenylpentanoate 
• 1334180-23-2 ethyl (R)-5-(allyloxy)-2-diazo-3-oxo-5-phenylpentanoate 
• 1334180-35-6 (R)-3-allyloxy-3-phenylpropanenitrile 

Downstream Products

• 287-23-0 cyclobutane 
• 862260-18-2 (24R)-epi-biyouyanagin A 
• 1046160-44-4 C₂₆H₂₈O₄ 
• 1046160-41-1 C₂₆H₃₀O₄ 
• 1046160-34-2 C₁₆H₁₆O₄ 
• 1046160-35-3 C₁₆H₁₆O₄ 
• 1242140-85-7 biyouyanagin B 
• 1242140-84-6 biyouyanagin C 
• 1242140-83-5 C₃₁H₃₈O₄ 
• 1242140-82-4 C₃₁H₃₈O₄ 
• 1242140-81-3 C₃₁H₃₈O₄ 

Relevant academic research and scientific papers

Synthesis of the anti-HIV agent (-)-hyperolactone C by using oxonium ylide formation-rearrangement

Starting from readily available (S)-styrene oxide an asymmetric synthesis is described of the naturally occurring anti-HIV spirolactone (-)-hyperolactone C, which possesses adjacent fully substituted stereocenters. The key step involves a stereocontrolled RhII-catalysed oxonium ylide formation-[2,3] sigmatropic rearrangement of an α-diazo-β-ketoester bearing allylic ether functionality. From the resulting furanone, an acid-catalysed lactonisation and dehydrogenation gives the natural product.

Biomimetic synthesis of hyperolactones

Through a biomimetic pathway, hyperolactone D, 4-hydroxyhyperolactone D, and hyperolactone C were synthesized from methyl acetoacetate via Weilers dianion method, asymmetric allylic alkylation, biomimetic lactonization, oxidation, and cyclization. The stereochemistry of the quaternary carbon was controlled efficiently by Palladium-catalyzed asymmetric allylic alkylation. This strategy was also used for the synthesis of hyperolactone B.

Construction of two vicinal quaternary carbons by asymmetric allylic alkylation: Total synthesis of hyperolactone C and (-)-biyouyanagin A

Call on triple A: Palladium-catalyzed asymmetric allylic alkylation (Pd-AAA; see scheme) has enabled a concise and efficient synthesis of hyperolacto ne C and (-)-biyouyanagin A in only six (20% Overall yield) and seven (8% overall yield) steps, respectively. The enantiomers of these natural products were also prepared by exploiting the same methodology.

Consecutive alkene cross-metathesis/oxonium ylide formation - Rearrangement: Synthesis of the anti-HIV agent hyperolactone C

(Chemical Equation Presented) α-Diazo-β-ketoesters bearing allylic ether functionality undergo highly stereoselective Ru-carbene-catalyzed alkene cross-metathesis followed by Rh2(OAc)4-catalyzed oxonium ylide formation/[2,3] sigmatropic rearrangement in a one-flask operation and in a highly diastereoselective manner. The methodology has been demonstrated in a concise synthesis of the anti-HIV agent hyperolactone C.

Total synthesis, revised structure, and biological evaluation of biyouyanagin A and analogues thereof

Isolated from Hypericum species H. Chinese L. var. salicifolium, biyouyanagin A was assigned structure 1a or 1b on the basis of NMR spectroscopic analysis. This novel natural product exhibited significant anti-HIV properties and inhibition of lipopolysacc

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.