Stereochemistry of terpene derivatives.: Part 5:: Synthesis of chiral lactones fused to a carane system -: insect feeding deterrents

被引:14
作者
Fraçkowiak, B
Ochalik, K
Bialonska, A
Ciunik, Z
Wawrzenczyk, C
Lochynski, S
机构
[1] Wroclaw Univ Technol, Fac Chem, Dept Bioorgan Chem, PL-50370 Wroclaw, Poland
[2] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
[3] Univ Agr, Dept Chem, PL-50375 Wroclaw, Poland
关键词
D O I
10.1016/j.tetasy.2005.11.025
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Chiral iodo- 9, bromo- 10 and hydroxylactones 12 condensed with the carane system were obtained. In each case, the synthetic pathway led to an enantiomerically pure diastereoisomer to generate two stereogenic centers. Iodo- 9 and bromolactone 10 possess a gamma-lactone group while the hydroxylactone 12 possesses a delta-lactone moiety situated trans to the gein-dimethylcyclopropyl ring. The structures of the products were confirmed by X-ray crystallography. These lactones were tested for antifeedant activity against storage pest insects. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:124 / 129
页数:6
相关论文
共 20 条
  • [1] BARDILI B, 1985, LIEBIGS ANN CHEM, P275
  • [2] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES
    BLASER, HU
    [J]. CHEMICAL REVIEWS, 1992, 92 (05) : 935 - 952
  • [3] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES
    BROWN, HC
    RANDAD, RS
    BHAT, KS
    ZAIDLEWICZ, M
    RACHERLA, US
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) : 2389 - 2392
  • [4] *BRUK AXS, 1999, SHELXTL V5 1
  • [5] FRACKOWIAK B, IN PRESS TETRAHEDRON
  • [6] GOLLNICK K, 1965, LIEBIGS ANN CHEM, V687, P14
  • [7] Synthesis and transformation of novel cyclic β-amino acid derivatives from (+)-3-carene
    Gyónfalvi, S
    Szakonyi, Z
    Fülöp, F
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (24) : 3965 - 3972
  • [8] A SIMPLE STEREOSELECTIVE VERSION OF CLAISEN REARRANGEMENT LEADING TO TRANS-TRISUBSTITUTED OLEFINIC BONDS . SYNTHESIS OF SQUALENE
    JOHNSON, WS
    WERTHEMANN, L
    BARTLETT, WR
    BROCKSOM, TJ
    LI, TT
    FAULKNER, DJ
    PETERSEN, MR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) : 741 - +
  • [9] Enantioselective addition of diethylzinc to aldehydes catalyzed by a β-amino alcohol derived from (+)-3-carene
    Joshi, SN
    Malhotra, SV
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (13) : 1763 - 1766
  • [10] An efficient chiral moderator prepared from inexpensive (+)3-carene: Synthesis of the HIV-1 non-nucleoside reverse transcriptase inhibitor DPC 963
    Kauffman, GS
    Harris, GD
    Dorow, RL
    Stone, BRP
    Parsons, RL
    Pesti, JA
    Magnus, NA
    Fortunak, JM
    Confalone, PN
    Nugent, WA
    [J]. ORGANIC LETTERS, 2000, 2 (20) : 3119 - 3121