165170-94-5

Basic information

• Product Name: 1,7-Dioxaspiro[4.4]non-2-ene-4,6-dione,9-ethenyl-9-methyl-2-phenyl-, (5S,9S)-
• Synonyms: 1,7-Dioxaspiro[4.4]non-2-ene-4,6-dione,9-ethenyl-9-methyl-2-phenyl-, trans-(-)-; (-)-Hyperolactone C; Hyperolactone C
• CAS NO: 165170-94-5
• Molecular Formula: C16H14 O4
• Molecular Weight: 270.285
• Mol File: 165170-94-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1,7-Dioxaspiro[4.4]non-2-ene-4,6-dione,9-ethenyl-9-methyl-2-phenyl-, (5S,9S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7-Dioxaspiro[4.4]non-2-ene-4,6-dione,9-ethenyl-9-methyl-2-phenyl-, (5S,9S)-(165170-94-5)
• EPA Substance Registry System: 1,7-Dioxaspiro[4.4]non-2-ene-4,6-dione,9-ethenyl-9-methyl-2-phenyl-, (5S,9S)-(165170-94-5)

Safety Data

• Hazardous Substances Data: 165170-94-5(Hazardous Substances Data)

Upstream product

• 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 
• 1334180-29-8 ethyl (R)-5-(allyloxy)-3-oxo-5-phenylpentanoate 
• 1289155-41-4 methyl (4R)-2-hydroxy-2-(2-hydroxy-2-phenylethyl)-4-methyl-4-vinyltetrahydrofuran-3-carboxylate 
• 1174170-63-8 3-hyproxyhyperolactone D 
• 1287702-06-0 (3S,4S)-3-hydroxy-3-(3-hydroxyl3-phenylpropanoyl)-4-methyl-4-vinyldihydrofuran-2(3H)-one 

Downstream Products

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

Relevant articles and documents

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.

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.

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