Structure and absolute configuration of a new rearranged chamigrane-type sesquiterpenoid from the sea hare Aplysia sp.

被引：14

作者：

Fedorov, SN ^{[1
]}

Shubina, LK ^{[1
]}

Kalinovsky, AI ^{[1
]}

Lyakhova, EG ^{[1
]}

Stonik, VA ^{[1
]}

机构：

[1] Russian Acad Sci, Pacific Inst Bioorgan Chem, Lab Chem Marine Nat Prod, Vladivostok 22, Russia

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 12期

关键词：

marine metabolites; terpenes; spectroscopy;

D O I：

10.1016/S0040-4039(00)00077-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(6S,10S)-3,10-Dimethyl-7,11-dimethylidenespiro[5,5]undec-2-en-4-one (1), a new rearranged chamigrane-type sesquiterpenoid with two sp(2)-hybridized carbons in alpha-positions to the spiro-atom, was isolated from the alcoholic extract of the sea hare Aplysia sp. and its structure and absolute configuration were established by chemical transformations, NMR, EIMS, IR, UV and CD spectroscopy. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1979 / 1982

页数：4

共 19 条

[1] A REARRANGED CHAMIGRENE DERIVATIVE AND ITS POTENTIAL BIOGENETIC PRECURSOR FROM A NEW SPECIES OF THE MARINE RED ALGAL GENUS LAURENCIA (RHODOMELACEAE) [J].

BITTNER, ML ;

SILVA, M ;

PAUL, VJ ;

FENICAL, W .

PHYTOCHEMISTRY, 1985, 24 (05) :987-989

[2] CHAMIGRANE METABOLITES FROM A JAMAICAN VARIETY OF LAURENCIA-OBTUSA [J].

BRENNAN, MR ;

ERICKSON, KL ;

MINOTT, DA ;

PASCOE, KO .

PHYTOCHEMISTRY, 1987, 26 (04) :1053-1057

[3] INTERESTING ASPECTS OF MARINE NATURAL-PRODUCTS CHEMISTRY [J].

FAULKNER, DJ .

TETRAHEDRON, 1977, 33 (12) :1421-1443

[4]

FEDOROV SN, 1990, DOKL AKAD NAUK SSSR, V307, P877

[5]

FENICAL W, 1979, RECENT ADV PHYTOCHEM, V13, P219

[6] Cartilagineol, the fourth lineage of Laurencia-derived polyhalogenated chamigrene [J].

Francisco, MEY ;

Turnbull, MM ;

Erickson, KL .

TETRAHEDRON LETTERS, 1998, 39 (30) :5289-5292

[7] THE CRYSTAL AND MOLECULAR-STRUCTURE OF 7,8-EPOXYHALOCHAMIGRENE [J].

FURUSAKI, A ;

KATAYAMA, C ;

MATSUMOTO, T ;

SUZUKI, M ;

SUZUKI, T ;

KIKUCHI, H ;

KUROSAWA, E .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (11) :3398-3402

[8] Stereochemical features of sesquiterpene metabolites as a distinctive trait of red seaweeds in the genus Laurencia [J].

Guella, G ;

Oztunc, A ;

Mancini, I ;

Pietra, F .

TETRAHEDRON LETTERS, 1997, 38 (47) :8261-8264

[9] Two new chamigranes from an Hawaiian red alga, Laurencia cartilaginea [J].

Juagdan, EG ;

Kalidindi, R ;

Scheuer, P .

TETRAHEDRON, 1997, 53 (02) :521-528

[10] CHAMIGRANE METABOLITES FROM LAURENCIA-OBTUSA AND LAURENCIA-SCOPARIA [J].

KENNEDY, DJ ;

SELBY, IA ;

THOMSON, RH .

PHYTOCHEMISTRY, 1988, 27 (06) :1761-1766

← 1 2 →