✦ LIBER ✦

The synthesis of 13-cis-retinoic acid-6,7-14C

✍ Scribed by Richard R. Muccino; Carol A. Wasiowich

Publisher: John Wiley and Sons
Year: 1980
Tongue: French
Weight: 290 KB
Volume: 17
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580170317

No coin nor oath required. For personal study only.

✦ Synopsis

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‐^14^C (6) and then condensed with acetone to give pseudoionone‐4,5‐^14^C (7). Ring closure of 7 gave β‐ionone‐6,^7^‐^14^C (8) which upon addition of vinyl Grignard give vinyl‐β‐ionol‐6,7‐^14^C (9). Conversion of 9 to its triphenylphosphonium salt 10 and condensation of the Wittig reagent from 10 with 4‐hydroxy‐3‐methylbut‐2‐enolide (11) gave a mixture from which pure 13‐cis‐retinoic acid‐6,7‐^14^C (1) could be crystallized.

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