735287-46-4

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 89186-81-2 1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene 
• 591-50-4 iodobenzene 
• 917251-09-3 tert-butyl-dimethyl-{3-phenyl-1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-allyloxy}-silane 
• 917251-07-1 (3R)-1-phenyl-5-(tetrahydro-2H-2-pyranyloxy)-1-pentyl-3-ol 
• 917251-08-2 1-phenyl-5-(tetrahydro-pyran-2-yloxy)-pent-1-en-3-ol 
• 917251-10-6 3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pent-4-en-1-ol 
• 917251-11-7 (3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal 
• 917251-14-0 5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-7-phenyl-hept-6-enoic acid ethyl ester 
• 6148-64-7 ethyl potassium malonate 
• 101979-49-1 (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one 

Downstream Products

• 500-64-1 Kavain 
• 173654-23-4 (R)-6-((E)-Styryl)-dihydro-pyran-2,4-dione 
• 70633-84-0 C₁₅H₂₀O₄ 
• 1271726-68-1 ethyl 2-((4R,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate 
• 1271726-69-2 2-((4R,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetaldehyde 
• 1271726-70-5 C₂₀H₂₆O₄ 
• 1271726-71-6 (E)-4-((4S,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)but-2-enal 
• 1271726-72-7 C₂₁H₂₈O₃ 
• 1271726-73-8 C₂₄H₃₀O₄ 
• 160098-78-2 (6R)-5,6-dihydro-6-[(4'S*,6'R*,1'E,7'E)-4',6'-dihydroxy-8'-phenyl-1',7'-octadienyl]-2-pyrone 

Relevant academic research and scientific papers

Total synthesis of cryptomoscatone F1 through an asymmetric aldol approach

A stereoselective total synthesis of naturally occurring styryl lactone, cryptomoscatone F1 is described. A Mukaiyama asymmetric aldol reaction, Brown's asymmetric allylation, Maruoka asymmetric allylation, and cross metathesis were used as the key steps.

Total synthesis of (-)-diospongin A and (+)-cryptofolione via asymmetric aldol reaction

Stereoselective synthesis of two distinctive pyranone skeletons diospongin A and cryptofolione has been described based on an asymmetric aldol reaction starting from Chan's diene. The synthetic strategy involves the enantioselective Mukaiyama aldol, diast

Application of the Cosford cross-coupling protocol for the stereoselective synthesis of (R)-(+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain

An efficient and versatile synthetic method has been developed and utilized for the stereoselective synthesis of (R)-(+)-goniothalamin 1, (R)-(+)-kavain 2 and (S)-(+)-7,8-dihydrokavain 3. Application of the Cosford protocol and direct conversion of aldehydes to β-keto-esters are the key steps in our approach.

Chemoenzymatic synthesis of enantiomerically enriched kavalactones

Lipase-mediated kinetic resolution of methyl-3-hydroxy-5-phenylpentanoate and (6E)-ethyl 5-hydroxy-3-oxo-7-phenylhept-6-enoate is described in high enantiomeric excess and good yields. The effect of different lipases in different solvents has been screened using different acylating agents. This protocol has been extended for the preparation of enantiomerically pure biologically important kavalactones.

Versatile asymmetric synthesis of the kavalactones: First synthesis of (+)-kavain

(Equation Presented) Three asymmetric pathways to the kavalactones have been developed. The first method is chiral auxiliary-based and utilizes aldol reactions of N-acetyl thiazolidinethiones followed by a malonate displacement/decarboxylation reaction. The second approach uses the asymmetric catalytic Mukaiyama additions of dienolate nucleophile equivalents developed by Carreira and Sato. Finally, tin-substituted intermediates, prepared by either of these routes, can serve as advanced general precursors of kavalactone derivatives via Pd(0)-catalyzed Stille couplings with aryl halides.