Synthesis of heliannane skeletons.: Facile preparation of (±)-heliannuol D

被引:46
作者
Macías, FA [1 ]
Chinchilla, D [1 ]
Molinillo, JMG [1 ]
Marín, D [1 ]
Varela, RM [1 ]
Torres, A [1 ]
机构
[1] Univ Cadiz, Dept Quim Organ, Grupo Alelopatia, Cadiz 11510, Spain
关键词
heliannane skeleton; Helianthus annuus; heliannuol; allelochemicals; synthesis of sesquiterpenes;
D O I
10.1016/S0040-4020(03)00134-0
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
Heliannuol D is a natural product with a 7, 10-heliannane skeleton, isolated from Helianthus annuus. It has been synthesized in eight steps, in good yield, using a new biomimetic method. Key steps were a Fries rearrangement, a Grignard reaction and, finally, a base catalyzed cyclization. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1679 / 1683
页数:5
相关论文
共 28 条
[1]
SIMPLE PROCEDURE FOR EPOXIDATION OF ACID-SENSITIVE OLEFINIC COMPOUNDS WITH META-CHLOROPERBENZOIC ACID IN AN ALKALINE BIPHASIC SOLVENT SYSTEM [J].
ANDERSON, WK ;
VEYSOGLU, T .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12) :2267-2268
[2]
Synthetic utility and mechanistic implications of the fries rearrangement of hydroquinone diesters in boron trifluoride complexes [J].
Boyer, JL ;
Krum, JE ;
Myers, MC ;
Fazal, AN ;
Wigal, CT .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) :4712-4714
[3]
DUKE S O, 1986, Reviews of Weed Science, V2, P15
[4]
Duke S. O., 1986, The science of allelopathy, P287
[5]
DUKE SO, 1997, P WEEDS 1997 BRIGHT, V2, P579
[6]
TOTAL SYNTHESIS OF (+/-)-HELIANNUOL-A [J].
GRIMM, EL ;
LEVAC, S ;
TRIMBLE, LA .
TETRAHEDRON LETTERS, 1994, 35 (37) :6847-6850
[7]
2 NEW METABOLITES, SYDONIC ACID AND HYDROXYSYDONIC ACID, FROM ASPERGILLUS-SYDOWI [J].
HAMASAKI, T ;
NAGAYAMA, K ;
HATSUDA, Y .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1978, 42 (01) :37-40
[8]
The structure and probable biogenesis of helianane, a heterocyclic sesquiterpene, from the Indo-Pacific sponge Haliclona ?fascigera [J].
Harrison, B ;
Crews, P .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2646-2648
[9]
Potential allelopathic activity of natural plant heliannanes:: A proposal of absolute configuration and nomenclature [J].
Macías, FA ;
Varela, RM ;
Torres, A ;
Molinillo, JMG .
JOURNAL OF CHEMICAL ECOLOGY, 2000, 26 (09) :2173-2186
[10]
MACIAS FA, 1995, ACS SYM SER, V582, P310