106231-29-2

Basic information

• Product Name: (-)-Rubifolide
• Synonyms: (-)-Rubifolide;(2Z,5R,11S)-3,14-Dimethyl-11-(1-methylethenyl)-6,16-dioxatricyclo[11.2.1.15,8]heptadeca-2,8(17),13,15(1)-tetren-7-one;(2Z,5S,11R)-3,14-Dimethyl-11-(1-methylethenyl)-6,16-dioxatricyclo[11.2.1.15,8]heptadeca-2,8(17),13,15(1)-tetren-7-one
• CAS NO: 106231-29-2
• Molecular Formula: C20H24O3
• Molecular Weight: 312.40276
• Mol File: 106231-29-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-Rubifolide(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Rubifolide(106231-29-2)
• EPA Substance Registry System: (-)-Rubifolide(106231-29-2)

Safety Data

• Hazardous Substances Data: 106231-29-2(Hazardous Substances Data)

Upstream product

• 201742-79-2 (-)-bipinnatin J 
• 912344-25-3 (S)-3-((E)-5-hydroxy-4-methyl-pent-3-enyl)-5-((Z)-3-iodo-2-methyl-allyl)-5H-furan-2-one 
• 912344-22-0 5-{(Z)-3-[(S)-4-((E)-5-hydroxy-4-methyl-pent-3-enyl)-5oxo-2,5-dihydro-furan-2-yl]-2-methyl-propenyl}-3-methyl-furan-2-carbaldehyde 
• 912344-26-4 5-{(Z)-3-[(S)-4-((E)-5-bromo-4-methyl-pent-3-enyl)-5-oxo-2,5-dihydro-furan-2-yl]-2-methyl-propenyl}-3-methyl-furan-2-carbaldehyde 
• 918313-67-4 3-[(S)-5-((Z)-3-iodo-2-methylallyl)-2-oxo-2,5-dihydro-furan-3-yl]-propionaldehyde 
• 918313-73-2 (E)-5-[(S)-5-((Z)-3-iodo-2-methylallyl)-2-oxo-2,5-dihydro-furan-3-yl]-2-methyl-pent-2-enal 
• 918313-68-5 (E)-5-[(S)-5-((Z)-3-iodo-2-methylallyl)-2-oxo-2,5-dihydro-furan-3-yl]-2-methyl-pent-2-enoic acid ethyl ester 
• 1219042-07-5 19-hydroxyrubifolide 

Relevant articles and documents

Exploring biosynthetic relationships among furanocembranoids: Synthesis of (-)-bipinnatin J, (H-)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B

(Diagram presented) The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed.

Total synthesis of coralloidolides A, B, C, and E

"Chemical Equation Presented" Mapping the matrix: Several coralloidolides, members of a Mediterranean branch of the furanocembranoid family of diterpenes, have been synthesized. The total syntheses include biomimetic transformations that often occur with high chemoselectivity, thus obviating the need for protecting-group manipulations. The fascinating reactivity of 2,5-diene-1,4dione moieties was explored in detail.

Synthesis of exo enol ether-cyclic ketal isomers of substituted furanmethanol structures related to marine furanocembranoids

Oxidations of the 2-alkenylfurans 8a and 8b, using peroxy reagents, lead to the dienedione 9 and the furan epoxide 10, respectively. Treatment of the epoxide 10 with p-TSA in MeOH produces the enol ether cyclic ketal 12, which is rapidly isomerised to the furanmethanol ether 15, isolated in 80% yield. By contrast, when the propanol-substituted furan epoxide 23 was kept in CDCl3 containing traces of HCl for 2 h, a 3:2 mixture of Z- and E-isomers of the enol ether spiro ketals 25a and 25b was produced in >92% yield; after 24 h this mixture of isomers underwent dehydration leading to the corresponding enol ether triene 26 (70%). When a solution of the dienedione 9 in H2O-THF containing p-TSA was stirred at 25 °C for 20 h, the tertiary alcohol 27 was produced which, after a further 20 h was converted into the furan vicinal diol 29. Likewise, when the 'cembranoid' dienedione 31 was treated with p-TSA-H2O, the hydroxymethyl-substituted furanobutenolide 33 was produced in 40% yield. It is probable that the enol ether cyclic hemiketals 28 and 32/34, which are related to 12 and 25, and also to the naturally occurring cembranoids 1 and 2 found in corals, are transient intermediates in the conversions leading to 29 and 33 from 9 and 31, respectively.