Chemical properties of marine terpenoids 1.: Some reactions of (6S,10R)-10-bromo-3,11,11-trimethyl-7-methylidenespiro[5,5]undec-2-en-4-one, a sesquiterpenoid from the sea hare Aplysia dactylomela

被引:7
|
作者
Lyakhova, EG [1 ]
Fedorov, SN [1 ]
Shubina, LK [1 ]
Radchenko, OS [1 ]
Kalinovsky, AI [1 ]
Dvitrenok, PS [1 ]
Stonik, VA [1 ]
机构
[1] Russian Acad Sci, Far Eastern Branch, Pacific Inst Bioorgan Chem, Vladivostok 690022, Russia
关键词
chamigrane-type sesquiterpenoids; terpenoids; CD spectra; mass spectrometry; H-1 and C-13 NMR spectra; mollusc; Opisthobranchia; sea hare; Aplysia dactylomela;
D O I
10.1023/A:1024489418232
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The structures of products obtained by reductive debromination and CF3COOH- and KOH-induced transformations of natural chamigrane-type sesquiterpenoid (6S,10R)-10-bromo-3,11,11-trimethyl-7-methylidenespiro[5,5]undec-2-en-4-one(dactylone) isolated from the sea hare Aplysia dactylomela were analyzed. The absolute configurations of the reaction products were established by CD spectra taking into account the configuration of the starting dactylone.
引用
收藏
页码:1022 / 1026
页数:5
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  • [1] Chemical properties of marine terpenoids. 1. Some reactions of (6S,10R)-10-bromo-3,11,11-trimethyl-7-methylidenespiro[5,5]undec-2-en-4-one, a sesquiterpenoid from the sea hare Aplysia dactylomela
    E. G. Lyakhova
    S. N. Fedorov
    L. K. Shubina
    O. S. Radchenko
    A. I. Kalinovsky
    P. S. Dvitrenok
    V. A. Stonik
    Russian Chemical Bulletin, 2003, 52 : 1022 - 1026
  • [2] ENANTIOSPECIFIC PREPARATION OF [(2R, 6S)-ENDO]-5-AZA-1,10,10-TRIMETHYL-3-OXATRICYCLO[5.2.1.0(2,6)]DECAN-4-ONE BY A NITRENE-MEDIATED ROUTE FROM [(1S)-ENDO]-(-)-BORNEOL AND ITS UTILITY AS A CHIRAL AUXILIARY IN SOME ASYMMETRIC TRANSFORMATIONS
    BANKS, MR
    BLAKE, AJ
    CADOGAN, JIG
    DAWSON, IM
    GOSNEY, I
    GRANT, KJ
    GAUR, S
    HODGSON, PKG
    KNIGHT, KS
    SMITH, GW
    STEVENSON, DE
    TETRAHEDRON, 1992, 48 (37) : 7979 - 8006