Synthesis of (1S,3R,5R,7S)-Sordidin,
the Main Component of the Aggregation Pheromone of the Banana Weevil Cosmopolites sordidus

Kamilla Lundhaug; Lars Skattebøl; Arne Jørgen Aasen

doi:10.1055/s-0028-1087373

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2009(1): 100-102
DOI: 10.1055/s-0028-1087373

LETTER

Synthesis of (1S,3R,5R,7S)-Sordidin, the Main Component of the Aggregation Pheromone of the Banana Weevil Cosmopolites sordidus

Kamilla Lundhaug^a, Lars Skattebøl*^b, Arne Jørgen Aasen^a
^a School of Pharmacy, University of Oslo, P.O. Box 1068, 0316 Oslo, Norway
^b Department of Chemistry, University of Oslo, P.O. Box 1033, 0315 Oslo, Norway
Fax: +47(22)85507; e-Mail: lars.skattebol@kjemi.uio.no;

Further Information

Publication History

Received 27 August 2008
Publication Date:
12 December 2008 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A synthesis of the banana weevil pheromone component (1S,3R,5R,7S)-sordidin starting from (S)-2-(2-ethyl-1,3-dioxolanyl)propan-1-ol and (R)-4-hydroxypentan-2-one is described. No epimerization was observed for the final, intramolecular, acid-catalyzed cyclization step using aqueous oxalic acid.

Key words

pheromone - enzymatic resolution - Grignard reaction - diastereoselectivity

References and Notes

1 Gold CS. Pinese B. Pena JE. In Tropical Fruit Pests and Pollinators: Biology, Economic Importance, Natural Enemies and Control Pena JE. Sharp J. Wysoki M. Cabi Publishing; University of Florida USA: 2002. p.13-56

Google Scholar
2 Budenberg WJ. Ndiege IO. Karago FW. J. Chem. Ecol. 1993, 19: 1905

Crossref Google Scholar
3 Beauhaire J. Ducrot P.-H. Malosse C. Rochat D. Ndiege IO. Otieno DO. Tetrahedron Lett. 1995, 36: 1043

Crossref Google Scholar
4 Mori K. Nakayama T. Takikawa H. Tetrahedron Lett. 1996, 37: 3741

Crossref Google Scholar
5 Nakayama T. Mori K. Liebigs Ann./Recl. 1997, 1075

Google Scholar
6 Ndiege IO. Jayaraman S. Oehlschlager AC. Gonzalez L. Alpizar D. Falles M. Naturwissenschaften 1996, 83: 280

Google Scholar
7 Jayaraman S. Ndiege IO. Oehlschlager AC. Gonzalez LM. Alpizar D. Falles M. Budenberg WJ. Ahuya P. J. Chem. Ecol. 1997, 23: 1145

Crossref Google Scholar
8 Ducrot P.-H. Synth.Commun. 1996, 26: 3923

Google Scholar
9 Fletcher MT. Moore CJ. Kitching W. Tetrahedron Lett. 1997, 38: 3475

Crossref Google Scholar
10 Wardrop DJ. Forslund RE. Tetrahedron Lett. 2002, 43: 737

Crossref Google Scholar
11 Wardrop DJ. Forslund RE. Landrie CL. Velter A.-I. Wink D. Surve B. Tetrahedron: Asymmetry 2003, 14: 929

Crossref Google Scholar
12 Yadav JS. Reddy KB. Prasad AR. Rehman HU. Tetrahedron 2007, 64: 2063

Google Scholar
13 Enders D. Breuer I. Nühring A. Eur. J. Org. Chem. 2005, 2677

Crossref Google Scholar
14 Ponaras AA. Tetrahedron Lett. 1976, 3105

Crossref Google Scholar
15 Rieke RD. Li PT.-J. Burns TP. Uhm ST. J. Org. Chem. 1981, 46: 4323

Crossref Google Scholar
16 Imamoto T. Takiyama N. Nakamura K. Tetrahedron Lett. 1985, 26: 4763

Crossref Google Scholar
17 Knochel P. Singer RD. Chem. Rev. 1993, 93: 2117

Crossref Google Scholar
18 Evans DA. Ennis MD. Le T. J. Am. Chem. Soc. 1984, 106: 1154

Crossref Google Scholar
19 Penning TD. Djuric SW. Haack RA. Kalish VJ. Miyashiro JM. Rowell BW. Yu SS. Synth. Commun. 1990, 20: 307

Crossref Google Scholar
21a Barros MT. Geraldes CFGC. Maycock CD. Silva MI. Tetrahedron 1988, 44: 2283

Google Scholar
21b Stahl I. Manske R. Gosselck J. Chem. Ber. 1980, 113: 800

Google Scholar
22 Anthonsen T. Hoff BH. Hofsløkken NU. Skattebøl L. Sundby E. Acta Chem. Scand. 1999, 53: 360

Crossref Google Scholar
23 Bernardi R. Ghiringhelli D. J. Org. Chem. 1987, 52: 5021

Crossref Google Scholar

20

The ee was determined by GC using a CP Chirasil-DEX CB (25 m × 0.25 mm, 0.25 µm film thickness) fused silica capillary column at isothermic temperatures.

24

Spectroscopic Data for 1a
^¹H NMR (300 MHz, CDCl₃): δ = 0.96 (d, J = 7.0 Hz, 3 H), 0.96 (t, J = 7.5 Hz, 3 H), 1.14 (d, J = 6.1 Hz, 3 H), 1.28 (s,
3 H), 1.18-1.35 (m, 3 H), 1.65 (m, 2 H), 2.13 (dd, J = 8.4, 12.4 Hz, 1 H), 2.31 (m, 1 H), 3.93 (m, 1 H). ^¹³C NMR (75 MHz, CDCl₃): δ = 8.0, 19.9, 21.9, 26.5, 27.4, 40.1, 44.1, 44.9, 64.5, 78.7, 108.6.