Intramolecular SN2 ring opening of a cyclic sulfate: synthesis of erythro-(−)-6-acetoxy-5-hexadecanolide—a major component of mosquito oviposition attractant pheromone

✍ Scribed by Braj B. Lohray; S. Venkateswarlu

• Book ID: 104361041
• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 398 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00011-6

✦ Synopsis

Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-ct followed by treatment with thionyl chloride to furnish cyclic sulfite 8 as the major product. The cyclic sulfite 8 is oxidized to the cyclic sulfate 2. Highly regio-and stereospecific ring opening of (4S,5S)-carboxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acetylation of 9 afforded natural oviposition attractant pheromone 1 in good yield. (~) 1997 Elsevier Science Ltd. All rights reserved.