22391-28-2

Upstream product

• 539-52-6 perillene 
• 22391-29-3 (E)-5-(furan-3-yl)-2-methylpent-2-en-1-ol 
• 56859-92-8 3-(3-furanyl)propan-1-ol 
• 56859-93-9 3-(furan-3-yl)propionaldehyde 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 43161-11-1 5-iodo-2-methylpent-2-ene 
• 56694-89-4 5-(3,6-Dihydro-[1,2]dioxin-4-yl)-2-methyl-pent-1-en-3-ol 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 107612-86-2 Methyl (2E)-5-(3-furyl)-2-methylpent-2-enoate 
• 870-63-3 prenyl bromide 
• 54355-98-5 trans-3-(3'-Furanyl)prop-2-en-1-ol 
• 180334-02-5 (E)-5-(furan-3-yl)-2-methylpent-2-enoic acid ethyl ester 
• 39244-10-5 (E)-3-furan-3-yl-acrylic acid 
• 56694-87-2 2-methyl-6-(3-furyl)-3-hydroxyhex-1-ene 

Relevant academic research and scientific papers

Efficient construction of benzohydrindenones from aryltrienones via domino Nazarov electrocyclization - Electrophilic aromatic substitution

1,4-Dien-3-ones substituted with pendant arylethyl side chains attached at C-1 were readily prepared from substituted dihydrocinnamaldehydes. Treatment with TiCl4 at low temperature effected domino Nazarov electrocyclization - arene trapping within 5 min to give racemic benzohydrindenones in near-quantitative yield and with complete diastereoselectivity.

Highly efficient trapping of the Nazarov intermediate with substituted arenes.

1,4-Dien-3-ones bearing pendant arylethyl side chains were readily prepared from substituted dihydrocinnamaldehydes. When treated with TiCl(4) at low temperature, these compounds underwent domino cyclization to give benzohydrindenones in near-quantitative yield and with complete diastereoselectivity. Reaction: see text.

New aspects in the synthesis of mono- and dialkylfurans

3-substituted furan systems can be obtained by alkylation of 3-lithium furans with various electrophiles in the presence of hexamethylphosphoric acid triamide in good yields. The 2- or 5-position of 3-methyl furan is blocked with high regio selectivity by silylation. After metalation and alkylation of the remaining free α-position and subsequent desilylation the 2,3- and 2,4-disubstituted furans are obtained. These methods are used to synthesize the naturally occuring compounds ursinanolide (2) and longifolin (4).

A CONVENIENT SYNTHESIS OF PERILLENAL

A convenient synthesis of chemically and stereoisomerically pure trans-perillenal is described.The compound has been prepared according to a simple procedure from methyl (2E)-5-(3-furyl)-2-methylpent-2-enoate obtained by alkylation of copper dienolate of tiglic or angelic acid with 3-(bromomethyl)furan.

Photooxidation with Simultaneous Reduction of Hydroperoxides with Tetrabutylammonium Borohydride. Synthesis of Perillenal from Myrcene

The synthetic routes to 2-methyl-5-(3-furyl)-2-pentenal, perillenal (1), starting from 2-methyl-6-methylene-2,7-octadiene, myrcene (2), are described.Myrcene (2) was either photooxidized to a mixture of the allylic alcohols 3 and 4 or converted to the aldehyde 11 by oxidation with selenium dioxide followed by chromium trioxide dipyridine in acetic acid.The alcohols 3 and 4 and the aldehyde 11 were cyclized with singlet oxygen to the endoperoxides 5, 6, and 12, respectively.The endoperoxides were converted to the furans 7, 8, and 1 by treatment with Fe(II).The secondary allylic furan 8 was converted to perillenal (1) by a one-step reaction involving an allylic rearrangement and an oxidation with pyridinium chlorochromate in the presence of p-toluenesulfonic acid in dichloromethane.A method for photooxidation and simultaneous reduction of hydroperoxides with tetrabutylammonium borohydride is presented.