167782-17-4

Upstream product

• 112775-69-6 (-)-(3S,4S,5S)-3,4-epoxy-5-methyldihydro-2(3H)-furanone 
• 74844-86-3 (E)-7-hydroxy-2-methyl-hept-2-enoic acid ethyl ester 
• 17642-18-1 methyl bromo-crotonate 
• 207127-93-3 methyl (2E,3E,5E)-2-ethylidene-9-oxo-4-methylnona-3,5-dienoate 
• 207127-96-6 (3E,5E,9E)-12-Carbamoyl-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-dodeca-3,5,9-trienoic acid methyl ester 
• 493001-76-6 (2E,4E)-tert-butyl 9-(tert-butyl-dimethylsiloxy)-4-methyl-nona-2,4-dienate 
• 479092-37-0 (3E,5E)-tert-butyl [(2E)-ethylidene]-9-hydroxy-4-methyl-nona-3,5-dienate 
• 479092-38-1 (3E,5E)-tert-butyl [(2E)-ethylidene]-4-methyl-9-formyl-octa-3,5-dienate 
• 207127-86-4 (E)-ethyl 7-(tert-butyl-dimethylsiloxy)-2-methyl-2-heptenate 
• 207127-88-6 (E)-7-(tert-butyl-dimethylsiloxy)-2-methyl-hept-2-enal 
• 207127-87-5 (E)-7-(tert-butyl-dimethylsiloxy)-2-methylhept-2-en-1-ol 
• 1027579-87-8 (3E,5E,9E)-11-[(2R,3S)-2-Cyano-3-((S)-1-hydroxy-ethyl)-oxiranyl]-2-eth-(E)-ylidene-4,10-dimethyl-11-oxo-undeca-3,5,9-trienoic acid methyl ester 
• 493001-80-2 (3E,5E,9E)-tert-butyl 12-cyano-[(2E)-ethylidene]-4,10-dimethyl-11-oxo-dodeca-3,5,9-trienoate 
• 493001-78-8 (3E,5E)-tert-butyl 9-(tert-butyl-dimethylsiloxy)-[(2E)-ethylidene]-4-methyl-nona-3,5-dienate 

Downstream Products

• 32381-28-5 N,N'-diacetyl-L-cystine dimethyl ester 
• 1038918-04-5 (2E,6E,8E,10E)-10-(methoxycarbonyl)-2,8-dimethyldodeca-2,6,8,10-tetraenoic acid 

Relevant academic research and scientific papers

Convergent total synthesis of epolactaene: Application of bridgehead oxiranyl anion strategy

Total synthesis of (+)-epolactaene was accomplished by a convergent approach utilizing the fluoride anion-catalyzed aldol-type reaction of (-)-α-trimethylsilylangelica lactone epoxide with tetraene aldehyde as a key reaction.

A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy

The generation and reaction of a lactone-derived oxiranyl anion is described. The aldol-type reaction of the epoxylactone and aldehydes was accomplished by a two-step procedure via the trimethylsilyl epoxylactone. The application of this methodology to th

Diastereoselective total synthesis of both enantiomers of epolactaene

A stereocontrolled total synthesis of both the (+)- and (-)-epolactaene ((+)- and (-)-1) enantiomers from tetrahydropyran-2-ol is described. The following reactions in this synthesis are particularly noteworthy: (1) the stereoselective construction of the conjugated (E,E,E)-triene by a combination of kinetic deprotonation and thermodynamic equilibration, (2) the E-selective Knoevenagel condensation of β-ketonitrile 33 with a chiral 2-alkoxyaldehyde, (3) a diastereoselective epoxidation achieved using a bulky nucleophile (TrOOLi) and an appropriate protecting group, (4) the mild hydrolysis of an α-epoxy nitrile by silica gel on TLC facilitated by hydroxyl-mediated, intramolecular assistance.

Asymmetric total synthesis of epolactaene. Part 2: Introduction of the side chain and synthesis of (+)-epolactaene and its enantiomer

A total synthesis of the novel neuritogenic agent (+)-epolactaene ((+)- 1) has been achieved via a convergent route that utilized epoxyamide 8, C7- C11 fragment 7, and C1-C6 Wittig reagent derived from phosphonium salt 19 followed by cyclization to form t

Asymmetric total synthesis of epolactaene

The first asymmetric total synthesis of epolactaene, a neuritogenic compound, was accomplished in 16 steps and its absolute stereochemistry was determined.