Synthesis of C-13-substituted retinoic acid analogs
✍ Scribed by Welch, Steven C.; Gruber, John M.
- Book ID
- 126205942
- Publisher
- American Chemical Society
- Year
- 1982
- Tongue
- English
- Weight
- 577 KB
- Volume
- 47
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
## Abstract Trans‐[13,14‐^14^C~2~]‐Retinoic acid has been synthesized by condensation of β‐ionylideneacetaldehyde and ^14^C‐labeled methyl senecioate in the presence of potassium amide in ether. A convenient synthesis of the key intermediate, methyl (diethoxyphosphinyl)‐[2‐^14^C]acetate, is also de
## 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**
## 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
## 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