141271-49-0

Basic information

• Product Name: (+/-)-anisomelic acid
• CAS NO: 141271-49-0
• Molecular Weight: 330.424
• Mol File: 141271-49-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+/-)-anisomelic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-anisomelic acid(141271-49-0)
• EPA Substance Registry System: (+/-)-anisomelic acid(141271-49-0)

Safety Data

• Hazardous Substances Data: 141271-49-0(Hazardous Substances Data)

Upstream product

• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 110965-93-0 (E)-6-{(2R,3R)-2-[(E)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pent-1-enyl]-5-methoxy-tetrahydro-furan-3-yl}-4-methyl-hex-3-en-1-ol 
• 110965-94-1 rel-(ξ,4S,5S)-4-<(E)-3-methyl-6-iodo-3-hexenyl>-5-<(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl>-2-methoxy-1-oxacyclopentane 
• 110965-92-9 rel-(2ξ,4S,5S)-4-<(E)-3-methyl-6-hydroxy-3-hexenyl>-5-<(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl>-2-methoxy-1-oxacyclopentane 
• 110965-91-8 rel-(2ξ,4R,5R)-4-<(E)-3-methyl-3,5-hexadienyl>-5-<(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl>-1-oxacyclopentan-2-ol 
• 116214-83-6 (E)-2-[Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-8-[(2R,3R)-5-methoxy-2-((E)-2-methyl-5-oxo-pent-1-enyl)-tetrahydro-furan-3-yl]-6-methyl-oct-5-enoic acid methyl ester 
• 110965-97-4 rel-(ξ,4S,5S)-4-<(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl>-5-<(E)-4-formyl-2-methyl-1-butenyl>-2-methoxy-1-oxacyclopentane 
• 110965-96-3 (E)-2-(Dimethoxy-phosphoryl)-8-[(2R,3R)-2-((E)-5-hydroxy-2-methyl-pent-1-enyl)-5-methoxy-tetrahydro-furan-3-yl]-6-methyl-oct-5-enoic acid methyl ester 
• 110966-00-2 (6E,10Z,14E)-(3aR,15aR)-3-Hydroxymethyl-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydro-1-oxa-cyclopentacyclotetradecene-10-carboxylic acid methyl ester 
• 110965-99-6 rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo<12.3.0>hexadeca-2,6,10-triene 
• 116214-85-8 (6E,10Z,14E)-(3aR,15aR)-2-Methoxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydro-1-oxa-cyclopentacyclotetradecene-10-carboxylic acid methyl ester 
• 116214-87-0 (6E,10Z,14E)-(3aR,15aR)-2-Hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydro-1-oxa-cyclopentacyclotetradecene-10-carboxylic acid methyl ester 
• 110965-89-4 N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate 
• 110965-84-9 (2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate 

Relevant articles and documents

CEMBRANOLIDE TOTAL SYNTHESIS. ANISOMELIC ACID

The stereoselective total synthesis of (+/-)-anisomelic acid (34) has been achieved starting from aldehyde 7, the ozonolysis product of geranyl acetate.Two key steps ensured the stereoselectivity of the synthesis.The first entailed a highly anti-selective addition of the allyltitanium derived from carbamate 15 to aldehyde 5 affording the enol carbamate allylic alcohol 16.The second was a highly (Z)-selective Horner-Emmons cyclization of the derived phosphono ester aldehyde 25 leading to the conjugated ester 27.Further conversion led to the crystalline lactone 30 whose structure was confirmed through single crystal X-ray analysis.Equilibration of the conjugated double bond of 30 gave rise to a 1:1 mixture of the (Z) and (E) isomers.This result was foretold by molecular mechanics calculations.