Total synthesis of a diastereomer of the marine natural product clavosolide A

被引:49
作者
Barry, CS
Bushby, N
Charmant, JPH
Elsworth, JD
Harding, JR
Willis, CL
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] AstraZeneca UK Ltd, Macclesfield SK10 4TG, Cheshire, England
关键词
D O I
10.1039/b509757f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first total synthesis of the reported structure of the sponge metabolite clavosolide A is described using a Prins cyclisation to assemble the tetrahydropyran core followed by manipulation of the side-chain, dimerisation and finally glycosidation.
引用
收藏
页码:5097 / 5099
页数:3
相关论文
共 12 条
[1]   Stereloselective synthesis of the tetrahydropyran core of polycarvernoside A [J].
Barry, CS ;
Bushby, N ;
Harding, JR ;
Willis, CL .
ORGANIC LETTERS, 2005, 7 (13) :2683-2686
[2]   DIASTEREOSELECTIVE CYCLOPROPANATION OF CHIRAL ALLYLIC ALCOHOLS - A MORE EFFICIENT REAGENT FOR THE RELATIVE STEREOCONTROL [J].
CHARETTE, AB ;
LEBEL, H .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :2966-2967
[3]   EFFICIENT AND MILD LACTONIZATION METHOD FOR SYNTHESIS OF MACROLIDES [J].
COREY, EJ ;
NICOLAOU, KC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5614-5616
[4]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[5]   Total synthesis and absolute configuration of polycavernoside A [J].
Fujiwara, K ;
Murai, A ;
Yotsu-Yamashita, M ;
Yasumoto, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10770-10771
[6]   CATALYTIC EFFECT OF NICKEL(II) CHLORIDE AND PALLADIUM(II) ACETATE ON CHROMIUM(II)-MEDIATED COUPLING REACTION OF IODO OLEFINS WITH ALDEHYDES [J].
JIN, H ;
UENISHI, J ;
CHRIST, WJ ;
KISHI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5644-5646
[7]   ENZYMATIC BETA-GALACTOSIDATION OF MODIFIED MONOSACCHARIDES - STUDY OF THE ENZYME SELECTIVITY FOR THE ACCEPTOR AND ITS APPLICATION TO THE SYNTHESIS OF DISACCHARIDES [J].
LOPEZ, R ;
FERNANDEZMAYORALAS, A .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :737-745
[8]   A MILD AND GENERAL-METHOD FOR THE SYNTHESIS OF O-GLYCOSIDES [J].
NICOLAOU, KC ;
SEITZ, SP ;
PAPAHATJIS, DP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2430-2434
[9]   Stereocontrolled elaboration of natural (-)-polycavernoside A, a powerfully toxic metabolite of the red alga Polycavernosa tsudai [J].
Paquette, LA ;
Barriault, L ;
Pissarnitski, D ;
Johnston, JN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) :619-631
[10]   Clavosolides A and B, dimeric macrolides from the Philippines sponge Myriastra clavosa [J].
Rao, MR ;
Faulkner, DJ .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (03) :386-388