𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Synthesis of 1-[13CD3]-9-cis-retinoic acid

✍ Scribed by Youssef L. Bennani

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
430 KB
Volume
36
Category
Article
ISSN
0022-2135

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

1‐[^13^CD~3~]‐9‐cis‐Retinoic acid was prepared in 8 steps from 2,6‐dimethylcyclohexanone. Alkylation of 2,6‐dimethylcyclohexanone under LiHMDS/MnBr~2~/^13^CD~3~I gave the corresponding labeled 2‐[^13^CD~3~]‐2,2,6‐trimethylcyclohexanone 4 in good yield. Further functionalization of 4 to 6‐[^13^CD~3~]‐β‐cyclocitral 6 proceeded through a Shapiro reaction. Aldehyde 6 was condensed with ethyl 3,3‐dimethylacrylate to afford the corresponding bicyclic pyranone 7. Reduction of 7 to lactol 8, followed by acid‐catalyzed ring opening gave the 9‐cis‐aldehyde 9. Wittig‐Horner olefination and saponification afforded the title compound in good overall yield and in excellent isotopic purity.

📜 SIMILAR VOLUMES

Synthesis of 13-cis-(11-3H)-retinoic aci
Synthesis of 13-cis-(11-3H)-retinoic acid
✍ Ping-Lu Chien; Ming-Sang Sung; David B. Bailey 📂 Article 📅 1979 🏛 John Wiley and Sons 🌐 French ⚖ 228 KB

## SYNTHESIS OF 13-e-(ll-3H)-RETINOIC ACID The b i o l o g i c a l a c t i v i t y of 1 3 -e -r e t i n o i c a c i d i n p r e v e n t i o n of e p i t h e l i a l cancer i n animals h a s r e c e n t l y been demonstrated [l]. I n c o n n e c t i o n w i t h a m e t a b o l i c s t u d i e s pro

The synthesis of 13-cis-retinoic acid-6,
The synthesis of 13-cis-retinoic acid-6,7-14C
✍ Richard R. Muccino; Carol A. Wasiowich 📂 Article 📅 1980 🏛 John Wiley and Sons 🌐 French ⚖ 290 KB

## Abstract A route to crystalline 13‐__cis__‐retinoic acid‐**6**,**7**‐^14^__C__ (**1**) has been developed. Addition of acetylene‐**1**,**2**‐^14^**C** to 6‐methyl‐5‐hepten‐2‐one (**4**) gave dehydrolinalool‐**1**,**2**‐^14^__C__ (**5**) which was catalytically transformed into citral‐**1**,**2**

Preparation of 9-cis-retinoic acid [11,1
Preparation of 9-cis-retinoic acid [11,12-3H(N)] by photochemical isomerization
✍ Marcia I. Dawson; Peter D. Hobbs; James F. Cameron; Sung W. Rhee 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 French ⚖ 163 KB

## Abstract All‐__trans__‐Retinoic acid [11,12‐^3^H(N)] was photochemically isomerized using a fluorescent source to afford a mixture of isomeric retinoic acids, from which 9‐__cis__‐retinoic acid[11,12‐^3^H(N)] was isolated by reversed‐phase HPLC. The identity of 9‐__cis__‐retinoic acid [11, 12‐^3

A preparation of high specific activity
A preparation of high specific activity [11,12-3H]-9-cis-retinoic acid
✍ Jotham W. Coe; Calvin R. Hawes; Patrick Towers 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 French ⚖ 429 KB

## Abstract A selective total synthesis of [11,12‐^3^H]‐9‐__cis__‐retinoic acid 1 at a specific activity of 46 Ci/mmole is described. The alkyne 4, efficiently prepared in two steps from readily available starting materials, was partially reduced to 9,11‐di‐__cis__‐retinoic acid 3 with both deuteri

Colorimetric determination of all-trans-
Colorimetric determination of all-trans-retinoic acid and 13-cis-retinoic acid
✍ Chih-Cheng Wang; Rupert E. Hodges Jr.; Donald L. Hill 📂 Article 📅 1978 🏛 Elsevier Science 🌐 English ⚖ 270 KB

A method employing trifluoroacetic acid for the quantitative determination ofallrrans-retinoic acid and 13-cis-retinoic acid in serum is described. The method permits the detection of as little as 0.3 Kg of either compound. Retinoic acid can serve the general tissue functions of vitamin A, except i

Simultaneous determination of all-trans,
Simultaneous determination of all-trans, 9-cis, 13-cis retinoic acid and retinol in rat prostate using liquid chromatography–mass spectrometry
✍ Yan Wang; William Y. Chang; Gail S. Prins; Richard B. van Breemen 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 294 KB 👁 1 views

## Abstract Since retinoic acid (RA) and RA receptors are key developmental regulators during organogenesis, they might participate in the abnormal development of the prostate caused by early estrogen exposure. In order to test this assumption, a sensitive analytical method that can differentiate 9