INTRAMOLECULAR S-N(2) RING-OPENING OF A CYCLIC SULFATE - SYNTHESIS OFERYTHRO-(-)-6-ACETOXY-5-HEXADECANOLIDE - A MAJOR COMPONENT OF MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE

Authors
LOHRAY BB VENKATESWARLU S
Citation
Bb. Lohray et S. Venkateswarlu, INTRAMOLECULAR S-N(2) RING-OPENING OF A CYCLIC SULFATE - SYNTHESIS OFERYTHRO-(-)-6-ACETOXY-5-HEXADECANOLIDE - A MAJOR COMPONENT OF MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE, Tetrahedron : asymmetry, 8(4), 1997, pp. 633-638
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
4
Year of publication
1997
Pages
633 - 638
Database
ISI
SICI code
0957-4166(1997)8:4<633:ISROAC>2.0.ZU;2-F
Abstract
Methyl trans-hexa-5-decenoate is dihydroxylated using AD-mix-alpha fol lowed by treatment with thionyl chloride to furnish cyclic sulfite 8 a s the major product. The cyclic sulfite 8 is oxidized to the cyclic su lfate 2. Highly regio- and stereospecific ring opening of (4S, 5S)-car boxybutyl-5-decylcyclic sulfate generated in situ by the hydrolysis of 2 furnished (5R,6S)-6-hydroxy-5-hexadecanolide 9 in high yield. Acety lation of 9 afforded natural oviposition attractant pheromone 1 in goo d yield. (C) 1997 Elsevier Science Ltd.