132971-61-0

Usage

InChI:InChI=1/C18H14O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-15-16-18(19)20-17/h2-3,8-16H,1H3/b3-2+,9-8+,11-10+,13-12+,17-14-

Upstream product

• 17090-98-1 all-trans-2,4,10-dodecatriene-6,8-diyn-1-al 
• 6214-35-3 (Z)-3-iodoprop-2-enoic acid 
• 259129-32-3 (3E,5E,7E,13E)-pentadeca-3,5,7,13-tetraene-1,9,11-triyne 
• 259129-36-7 (3E,5E,7E,13E)-1-(tert-butyldimethylsilyl)-3,5,7,13-pentadecatetraen-1,9,11-triyne 
• 811861-65-1 (3E,5E,7E,13E)-1-trimethylsilyl-pentadeca-3,5,7,13-tetraene-1,9,11-triyne 
• 811861-64-0 (5E)-1-trimethylsilyl-hept-5-ene-1,3-diyne 
• 168295-33-8 (2E,4E)-5-bromopenta-2,4-dienal 
• 61121-17-3 (5E)-hept-5-ene-1,3-diyne 

Relevant academic research and scientific papers

First synthesis of Xerulin, an inhibitor of the biosynthesis of cholesterol

Starting from L-ascorbic acid, crotonaldehyde, (trimethylsilyl)acetylene and the stannylated alcohol 15, the title compound 4 was synthesized for the first time. L-Ascorbic acid was elaborated into phosphonium bromide 19 with a high degree of Z-stereoselectivity while the other starting materials were combined for obtaining the unsaturated aldehyde 5. A Wittig reaction between this aldehyde and the ylide derived from bromide 19 provided xerulin (4) along with a mixture of isomers which was readily separable.

New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol

A new stereoselective methodology for the synthesis of both dihydroxerulin and xerulin has been devised. The key step required cross-coupling reactions between the bromo trienyne, (1E,3E,5E)-1-bromo-8-trimethylsilyl-1,3,5-octatrien- 7-yne and the appropriate conjugated diynes. The palladium-catalyzed tandem cross-coupling/cyclization reaction of the resulting polyenynes with (Z)-3-iodo-2-propenoic acid led directly to dihydroxerulin or xerulin with a high degree of stereoselectivity. A new stereoselective methodology has been devised for the total synthesis of both dihydroxerulin and xerulin.

An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-lodobromoethylene as a novel two-carbon synthon.

[structure: see text] Xerulin, an inhibitor of cholesterol biosynthesis, has been synthesized from commercially available (E)-1-bromopropene, acetylene, and propynoic acid in five steps (longest linear sequence) in 30% overall yield and >96% stereoselectivity. The preparation of (E)-iodobromoethylene and its use in the Pd-catalyzed cross coupling are two of the novel aspects of the synthesis reported herein.