cas 59632-76-7, (3aR,6E,10Z,14E,15aS)-2,3,3a,4,5,8,9,12,13,15a-Decahydro-6,14-dimethyl-3-methylene-2-oxocyclotetradeca[b]furan-10-carboxylic acid | Articles data ｜lookchem

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59632-76-7

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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.
Marshall, James A.,DeHoff, Bradley S.
p. 4849 - 4860
(2007/10/02)

STEREOSELECTIVE TOTAL SYNTHESIS OF THE CEMBRANOLIDE DITERPENE ANISOMELIC ACID
A highly stereoselective total synthesis of the cembranolide diterpene anosomelic acid has been achieved via a convergent route.Macrocyclization was effected by a (Z)-selective intramolecular Horner-Emmons condensation.
Marshall, James A.,DeHoff, Bradley S.
p. 4873 - 4876
(2007/10/02)

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105470-73-3
(rel-3Ξ,3aR)-(6E,10Z,14E)-6,14-dimethyl-2-oxo-(3ar,15at)-3a,4,5,8,9,12,13,15a-octahydro-spiro[cyclotetradeca[b]furan-3,3'-pyrazole]-10-carboxylic acid methyl ester

Chemical Properties

Boiling Point: 543.5oC at 760 mmHg
Flash Point:191.7oC
Density: 1.12g/cm3
Vapor Pressure: 2.97E-13mmHg at 25°C
Refractive Index: 1.544
PSA: 63.60000
LogP: 4.34200

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