28368-06-1

Upstream product

• 99647-32-2 3-methyl 5β-<2,6,6-trimethyl 5β-(4-hydroxy-3-methyl 2E-butenyl) 2-cyclohexenyl> 1,4-pentadien 3-ol (2-hydroxyprenyl vinyl α-cis-ionol) 
• 1838-94-4 isoprene epoxide 
• 99647-27-5 4β-<2,6,6-trimethyl 5β-(4-acetoxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-acetoxyprenyl α-cis-ionone) 
• 99647-24-2 4β-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 3E-buten 2-one (2-hydroxyprenyl α-cis-ionone) 
• 141-10-6 pseudoionone 
• 5056-17-7 (2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial 
• 99647-34-4 3-methyl 5β-<2,6,6-trimethyl 5β-(4-hydroxy 3-methyl 2E-butenyl) 2-cyclohexenyl> 1,4-pentadienyl triphenylphosphonium bromide (2-hydroxyprenyl α-cis-ionylidene ethyltriphenylphosphonium bromide) 

Relevant academic research and scientific papers

C45 und C50-Carotinoide. Synthese eines optisch aktiven cyclischen C20-Bausteins und von Decaprenoxanthin ( = (2R,6R,2'R,6'R)-2,2'-Bis(4-hydroxy-3-methylbut-2-enyl)-ε,ε-carotin)

The synthesis of the optically active cyclic C20-building block (R,R)-15 and of the optically active C50-carotenoid (2R,6R,2'R,6'R)-decaprenoxanthin (1) starting from (-)-β-pinene ((S)-2) is reported.

BIOMIMETIC SYNTHESIS OF BACTERIAL C50 CAROTENOIDS DECAPRENOXANTHIN AND C.p. 450

Alkylation of the distal double bond of pseudoionone 4 has been carried out with isoprene epoxide (ZnCl2/MeNO2) leading directly to α-cis 10a, α-trans 10b and γ 10c hydroxyprenylionones.The α-cis and γ-isomers have been converted in few steps into the C50 carotenoids decaprenoxanthin 1 and C.p. 450 3 respectively.