Synthesis and absolute configuration of sordidin, the male-produced aggregation pheromone of the banana weevil, Cosmopolites sordidus

Tetrahedron Letters

Volumn 37, Issue 21, 1996, Pages 3741-3744

  Mori, Kenji ^a   Nakayama, Tôru ^a   Takikawa, Hirosato ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PHEROMONE; SORDIDIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0029887366     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00674-0     Document Type: Article

References (10)

1. Budenberg, W. J.; Ndiege, I. O.; Karago, F. W. J. Chem. Ecol. 1993, 19, 1905-1916.
2. Beauhaire, J.; Ducrot, P.-H.; Malosse, C.; Rochat, D.; Ndiege, I. O.; Otieno, D. O. Tetrahedron Lett. 1995, 36, 1043-1046.
3. All the new compounds were characterized by spectroscopic (IR and NMR) and elemental (combustion or HRMS) analysis.
4. Eis, M. J.; Wrobel, J. E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693-3694.
5. +, 0.3).
6. GC conditions; preparative - PREPGC-TH (special GC) equipped with a PEG-20M, 10% on Uniport-HP (80-100 mesh), 100°C (constant), analysis - GC-14A equipped with a PEG-20M(0.25 mm i.d. × 60 m), 120°C (constant), chiral analysis - GC-14A equiped with a DMPBCD-TH {heptakis-(2,6-di-0-methyl-3-O-pentyl)-β-cyclodextrin}, 0.25 mm i.d. × 50 m, 70°C to 140°C (1.0°C/min).
7. 13C cosy and HMBC).
8. 2 = 184.1464, Found 184.1453.
9. Ditails of the bioassay of (±)-1 will be published separately by Prof. K. Jaffe in J. Chem. Ecol.
10. 2O).