51918-98-0

Basic information

• Product Name: teucvin
• Synonyms: teucvin;(3R,5S,5'aS)-5-(3-Furyl)-3',4,5,5',5'a,7',8',8'aβ-octahydro-7'α-methylspiro[furan-3(2H),6'-[6H]naphtho[1,8-bc]furan]-2,2'(4'H)-dione;(5aS,5'S,6R)-5'-(3-Furyl)-7α-methyl-3,4,4',5,5',5aβ,8,8aβ-octahydrospiro[2H-naphtho[1,8-bc]furan-6(7H),3'(2'H)-furan]-2,2'-dione
• CAS NO: 51918-98-0
• Molecular Formula: C19H20O5
• Molecular Weight: 328.3591
• Mol File: 51918-98-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: teucvin(CAS DataBase Reference)
• NIST Chemistry Reference: teucvin(51918-98-0)
• EPA Substance Registry System: teucvin(51918-98-0)

Safety Data

• Hazardous Substances Data: 51918-98-0(Hazardous Substances Data)

Upstream product

• 68370-49-0 montanin-A 
• 64756-04-3 19-acetylgnaphalin 
• 136176-62-0 (12S,20S)-7α-Acetoxy-20-O-acetyl-15,16-epoxy-19-norneoclerodane-4,13(16),14-triene 20,12-hemiacetal 6α,18-methyl acetal 
• 71774-90-8 eriocephalin 
• 136176-60-8 (12S,20S)-7α-Acetoxy-20-O-acetyl-15,16-epoxy-19-norneoclerodane-4,13(16),14-triene 6α,18;20,12-dihemiacetal 
• 136176-61-9 (12S,20S)-7α-Acetoxy-20-O-acetyl-6,18;15,16-diepoxy-19-norneoclerodane-4(18),5,13(16),14-tetraene 20,12-hemiacetal 
• 70544-90-0 gnaphalin 
• 77265-12-4 C₂₃H₂₆O₈ 
• 77265-11-3 C₂₁H₂₄O₇ 
• 136176-66-4 (12S)-15,16-Epoxy-19-norneoclerodane-4,13(16),14-trien-18,6α-olide 20,12-hemiacetal 
• 1378319-21-1 C₁₇H₂₂O₄ 
• 1378319-20-0 C₁₆H₂₀O₃ 
• 22037-28-1 3-bromofurane 
• 1378319-36-8 C₁₆H₂₀O₅ 

Relevant articles and documents

Transformation of Neoclerodane Diterpenoids into 19-Norneoclerodane Derivatives

The neoclerodane diterpenoid eriocephalin (1) was transformed into its 19-nor derivatives 3 and 4 by reaction with potassium tert-butoxide in THF, whereas with the same treatment compound 6 yielded only the transacetylation derivative 7.These results indicated that 19-acetoxy-4α,18-epoxy-7α-hydroxy-6-oxoneoclerodane derivatives are transformed into the corresponding 19-nor compounds in a retroaldol reaction by loss of the C-19 carbon as formaldehyde followed by opening of the oxirane ring and intramolecular attack by a C-18 alkoxide on the carbonyl C-6 carbon atom, giving the allylic hemiacetal 3, which is easily dehydrated to the furanic derivative 4.Compound 4 was transformed into the α,β-unsaturated γ,δ-enol γ-lactone 8 by an oxidation reaction with atmospheric oxygen in chloroform solution.Alternatively, it gave the α,β-unsaturated γ-lactone 11 under acid catalysis.These reactions allowed the partial syntheses of the naturally occurring diterpenoids teuscorolide (9) and teucvin (12) and are of interest for chemical transformations of substances of this kind.

Total synthesis of (-)-teucvidin

A concise enantioselective synthesis of (-)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia-ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol for construction of the fused furanone moiety, and the O-allylation/Claisen rearrangement protocol for construction of the all-carbon quaternary center at C9 of the clerodane skeleton.

MALLOTUCIN C AND D, TWO DITERPENIC LACTONES FROM MALLOTUS REPANDUS

Investigation on the constituents of the titled plant collected in June resulted in the isolation of mallotucin B and mallotucins C and D (as acetates).Mallotucin A (=teucvin), which is the only diterpenic constituent in the plant collected in December, was not detected.Structures of mallotucins C and D were elucidated on the basis of their chemical correlation with mallotucin A and the detailed spectral analyses of their acetates.Mallotucin A is suggested to be biosynthesized from chettaphane-type precursors, mallotucins B, C and/or D.