81026-38-2

Basic information

• Product Name: lobohedleolide
• Synonyms: lobohedleolide;(3aS,6E,10E,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;(7Z)-lobohedleolide
• CAS NO: 81026-38-2
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 0
• Mol File: 81026-38-2.mol

Chemical Properties

• Boiling Point: 543.5°C at 760 mmHg
• Flash Point: 191.7°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 2.97E-13mmHg at 25°C
• Refractive Index: 1.544
• CAS DataBase Reference: lobohedleolide(CAS DataBase Reference)
• NIST Chemistry Reference: lobohedleolide(81026-38-2)
• EPA Substance Registry System: lobohedleolide(81026-38-2)

Safety Data

• Hazardous Substances Data: 81026-38-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H26O4/c1-13-6-4-8-16(19(21)22)9-5-7-14(2)12-18-17(11-10-13)15(3)20(23)24-18/h6,9,12,17-18H,3-5,7-8,10-11H2,1-2H3,(H,21,22)/b13-6-,14-12-,16-9-/t17-,18?/m0/s1

Upstream product

• 80994-13-4 (+/-)-methyl anisomelate 
• 100045-80-5 (E)-6-((tert-butyldimethylsilyl)oxy)-3-methylhex-2-en-1-yl acetate 
• 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 
• 110965-93-0 (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 
• 35334-60-2 (E)-6-acetoxy-4-methyl-4-hexenal 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 100045-81-6 (E)-3-methyl-6-<(tert-butyldimethylsilyl)oxy>-2-hexen-1-ol 
• 116214-81-4 (E)-2-[Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-8-{(2R,3R)-2-[(E)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-1-enyl]-5-methoxy-tetrahydro-furan-3-yl}-6-methyl-oct-5-enoic acid methyl ester 
• 116214-90-5 (E)-2-[Bis-(2,2,2-trifluoro-ethoxy)-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 
• 110965-95-2 (E)-8-{(2R,3R)-2-[(E)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pent-1-enyl]-5-methoxy-tetrahydro-furan-3-yl}-2-(dimethoxy-phosphoryl)-6-methyl-oct-5-enoic acid methyl ester 
• 110965-90-7 anti-(1Z,5E)-1-(N,N-diisopropylcarbamoyloxy)-6-methyl-9-tert-butyldimethylsilyloxy-3-<(E)-3-methyl-3,5-hexadienyl>-1,5-nonadien-4-ol 
• 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 
• 100571-25-3 (E)-3-methyl-6-<(tert-butyldimethylsilyl)oxy>-2-hexenal 

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.

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.