𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthese und Chiralität der enantiomeren 6-Hydroxy-α-ionone sowie von cis- und trans-5,6-Dihydroxy-5,6-dihydro-β-iononen

✍ Scribed by Walter Eschenmoser; Peter Uebelhart; Conrad Hans Eugster

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
624 KB
Volume
64
Category
Article
ISSN
0018-019X

No coin nor oath required. For personal study only.

✦ Synopsis

Synthesis and Chirality of the Enantiomeric 6‐Hydroxy‐α‐ionones and of cis‐ and trans‐5,6‐Dihydroxy‐5,6‐dihydro‐β‐ionones

We describe the synthesis of (−)‐(5__R__,6__S__)‐5,6‐dihydroxy‐5,6‐dihydro‐β‐ionone (10) and (+)‐(5__S__,6__S__)‐5,6‐dihydroxy‐5,6‐dihydro‐β‐ionone (12). The absolute configuration of these compounds has been established by correlation with (R)‐4‐hydroxy‐β‐ionone (1).

Therefore, by comparison, the 5,6‐dihydroxy‐5,6‐dihydro‐β‐ionone recently isolated from Rehmannia glutinosa var. purpurea by Endo et al.[4] has the (5__R__,6__R__)‐configuration ((−)−12). The same holds for the 5‐β‐D‐glucopyranoside (15) isolated from Aeginetia indica var. gracilis.

📜 SIMILAR VOLUMES

Synthese von (-)-(R)-4-Hydroxy-β-ionon u
Synthese von (-)-(R)-4-Hydroxy-β-ionon und (-)-(5 R, 6 S)-5-Hydroxy-4,5-dihydro-α-ionon aus (-)-(S)-α-Ionon
✍ Andreas Haag; Walter Eschenmoser; Conrad Hans Eugster 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 German ⚖ 380 KB

**Synthesis of (‐)‐(__R__)‐4‐Hydroxy‐β‐ionone and (‐)‐(5 __R__, 6 __S__)‐5‐Hydroxy‐4,5‐dihydro‐α‐ionone aus (‐)‐(__S__)‐α‐Ionone** The absolute configuration of the chiral 4‐hydroxy‐β‐ionones and 5‐hydroxy‐4,5‐dihydro‐α‐ionones has been determined by chemical connection with (‐)‐(__S__)‐α‐ionone __

Synthese und Chiralität von (5S, 6R)-5,6
Synthese und Chiralität von (5S, 6R)-5,6-Epoxy-5,6-dihydro-β,β-carotin und (5R, 6R)-5,6-Dihydro-β,β-carotin-5,6-diol, einem Carotinoid mit ungewöhnlichen Eigenschaften
✍ Walter Eschenmoser; Conrad Hans Eugster 📂 Article 📅 1978 🏛 John Wiley and Sons 🌐 German ⚖ 555 KB

**Synthesis and Chirality of (5__S__,6__R__)‐5,6‐Epoxy‐5,6‐dihydro‐β,β‐carotene and (5__R__,6__R__)‐5,6‐Dihydro‐β,β‐carotene‐5,6‐diol, a Compound with Unexpected Solubility Characteristics** __Wittig__‐condensation of azafrinal (**1e**) with the phosphorane derived from **7** leads to a (1:3)‐mixtu

Synthese und Chiralität von (5R, 6R)-5,6
Synthese und Chiralität von (5R, 6R)-5,6-Dihydro-β, ψ-carotin-5,6-diol, (5R, 6R, 6′R)-5,6-Dihydro-β, ε-carotin-5,6-diol, (5S, 6R)-5,6-Epoxy-5,6-dihydro-β, ψ-carotin und (5S, 6R, 6′R)-5,6-Epoxy-5,6-dihydro-β,ε-carotin
✍ Walter Eschenmoser; Peter Uebelhart; Conrad Hans Eugster 📂 Article 📅 1979 🏛 John Wiley and Sons 🌐 German ⚖ 331 KB 👁 1 views

**Synthesis and Chirality of (5__R__, 6__R__)‐5,6‐Dihydro‐β, ψ‐carotene‐5,6‐diol, (5__R__, 6__R__, 6′__R__)‐5,6‐Dihydro‐β, ε‐carotene‐5,6‐diol, (5__S__, 6__R__)‐5,6‐Epoxy‐5,6‐dihydro‐β,ψ‐carotene and (5__S__, 6__R__, 6′__R__)‐5,6‐Epoxy‐5,6‐dihydro‐β,ε‐carotene** __Wittig__‐condensation of optically