2571-86-0

Usage

Uses

Coriamyrtin is not recommended for any applications due to its high toxicity and potential for causing severe harm or death. Exposure to coriamyrtin should be avoided to prevent any adverse effects.

Upstream product

• 90123-00-5 C₂₁H₃₆O₅Si 
• 90123-03-8 C₂₄H₄₂O₄Si 
• 90123-01-6 C₂₁H₃₆O₆Si 
• 90742-34-0 C₂₃H₄₀O₅Si 
• 90192-36-2 C₂₂H₃₈O₆Si 
• 81491-87-4 C₁₅H₁₉BrO₃ 
• 81491-94-3 (3aR,4S,5R,6S,7aR)-5-Isopropenyl-7a-methyl-1-oxo-3a,6-bis-(tetrahydro-furan-2-yloxy)-octahydro-indene-4-carboxylic acid methyl ester 
• 81491-85-2 (3aR,4S,5R,6S,7aS)-5-Isopropenyl-7a-methyl-1-methylene-3a,6-bis-(tetrahydro-furan-2-yloxy)-octahydro-indene-4-carboxylic acid methyl ester 
• 82614-37-7 C₁₆H₂₁BrO₇S 
• 81491-89-6 C₁₅H₁₉BrO₅ 
• 81491-88-5 C₁₅H₁₉BrO₄ 
• 81491-86-3 (1R,2S,6R,8R,11S)-2-Hydroxy-11-isopropenyl-6-methyl-5-methylene-9-oxa-tricyclo[6.2.1.0^2,6]undecan-10-one 
• 88567-34-4 (3aS,4R,5S,6R,7aR)-3a,6-Dihydroxy-5-isopropenyl-7a-methyl-1-methylene-octahydro-indene-4-carboxylic acid methyl ester 
• 88593-70-8 C₁₅H₁₉BrO₃ 

Relevant academic research and scientific papers

Stereocontrolled Total Synthesis of (-)-Picrotoxinin and (+)-Coriamyrtin via a Common Isotwistane Intermediate

Stereocontrolled total synthesis of (-)-picrotoxinin (1) and (+)-coriamyrtin (2), toxic sesquiterpenoids of plant origin, is described, utilizing isotwistane compounds as common and key intermediates.

Synthetic Studies on a Picrotoxane Sesquiterpene, Coriamyrtin. III. Completion of the Stereocontrolled Total Synthesis of (+/-)-Coriamyrtin

The stereocontrolled total synthesis of (+/-)-coriamyrtin (1) has now been completed, starting from protoanemonin and 2-methyl-1,3-cyclopentanedione, through fifteen steps.The Wittig reaction of the ditetrahydrofuranyl ether (3) with triphenylphosphonium methylide gave the exo-methylenic compound (4), which was derived to the lactone (6) by consecutive hydrolysis, alkaline hydrolysis, and lactonization.The lactone (6) was transformed into the bromoether (8), which was subjected to allylic hydroxylation to give the allyl alcohol (10).Epoxidation of the allyl alcohol (10) provided selectively the epoxy-alcohol (11), which was derived to the mesylate (16).Elimination of the O-mesyl group gave the olefin (17).Epoxidation of 17 with m-chloroperbenzoic acid gave (+/-)-bromocoriamyrtin (18) and finally, reductive debromination of 18 furnished (+/-)-coriamyrtin (1).Keywords - coriamyrtin synthesis; Wittig reaction; allylic hydroxylation; lactonization; bromination; elimination; debromination