Synthesis of haminol-A and haminol-B, polyenic alarm pheromones of Cephalaspidean molluscs

被引:9
作者
Alvarez, R [1 ]
de Lera, AR [1 ]
机构
[1] Univ Vigo, Dept Quim Fis & Quim Organ, Vigo 36200, Spain
关键词
D O I
10.1016/S0957-4166(98)00324-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Two stereocontrolled palladium-catalyzed cross-couplings of I-alkenyl boronic acids and aryl/alkenyl halides (the Suzuki-Miyaura reaction) are the key steps in an enantioselective approach to the polyene fragment of haminols A and B, alarm pheromones isolated from Haminoea navicula, a Cephalaspidean Opisthobranch mollusc. Chirality rested on the use of (S)-propylene oxide as the starting material. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3065 / 3072
页数:8
相关论文
共 37 条
[1]   Stereoselective synthesis of polyenic alarm pheromones of cephalaspidean molluscs [J].
Alvarez, R ;
Herrero, M ;
López, S ;
de Lera, AR .
TETRAHEDRON, 1998, 54 (24) :6793-6810
[2]  
Alvarez Rosana, 1995, Natural Product Letters, V6, P127, DOI 10.1080/10575639508044100
[3]   Synthesis of stipiamide and a new multidrug resistance reversal agent, 6,7-dehydrostipiamide [J].
Andrus, MB ;
Lepore, SD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) :2327-2328
[5]   ALARM PHEROMONES FROM THE MEDITERRANEAN OPISTHOBRANCH HAMINOEA-NAVICULA [J].
CIMINO, G ;
PASSEGGIO, A ;
SODANO, G ;
SPINELLA, A ;
VILLANI, G .
EXPERIENTIA, 1991, 47 (01) :61-63
[6]  
COTTERILL SA, 1995, J CHEM SOC P1, P1215
[7]   EXPERIMENTAL AND THEORETICAL-ANALYSIS OF THE STERIC TOLERANCE OF THE BINDING-SITE OF BACTERIOOPSIN WITH THE USE OF SIDE-CHAIN METHYL-SHIFTED RETINAL ANALOGS [J].
DELERA, AR ;
IGLESIAS, B ;
RODRIGUEZ, J ;
ALVAREZ, R ;
LOPEZ, S ;
VILLANUEVA, X ;
PADROS, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (31) :8220-8231
[8]   The first stereospecific approach to both enantiomers of mellein [J].
Dimitriadis, C ;
Gill, M ;
Harte, MF .
TETRAHEDRON-ASYMMETRY, 1997, 8 (13) :2153-2158
[9]   TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC RUTAMYCIN-B [J].
EVANS, DA ;
NG, HP ;
RIEGER, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11446-11459
[10]   MARINE NATURAL-PRODUCTS [J].
FAULKNER, DJ .
NATURAL PRODUCT REPORTS, 1992, 9 (04) :323-364