Synthesis of the alleged structure of sclerophytin A. The setting of two oxygen bridges within the fused cyclodecanol B ring is not nature's way

被引:54
作者
Paquette, LA [1 ]
Moradei, OM [1 ]
Bernardelli, P [1 ]
Lange, T [1 ]
机构
[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA
关键词
D O I
10.1021/ol000083o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structure attributed to sclerophytin A, a cytotoxic soft coral metabolite, was synthesized in an enantioselective manner from (5S)-5-(d-menthyloxy)-2(5H)-furanone. The spectral properties and polarity of the synthetic product require that the structural assignment to the natural material be revised.
引用
收藏
页码:1875 / 1878
页数:4
相关论文
共 40 条
[1]   SCLEROPHYTIN C-F - ISOLATION AND STRUCTURES OF 4 NEW DITERPENES FROM THE SOFT CORAL SCLEROPHYTUM-CAPITALIS [J].
ALAM, M ;
SHARMA, P ;
ZEKTZER, AS ;
MARTIN, GE ;
JI, XH ;
VANDERHELM, D .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1896-1900
[2]   Stereoselective indium-promoted allylation of gamma-hydroxy-gamma-lactones under aqueous conditions. The neighboring carboxyl effect [J].
Bernardelli, P ;
Paquette, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8284-8285
[3]  
Bernardelli P, 1998, HETEROCYCLES, V49, P531
[4]  
BERNARDELLI P, 1997, THESIS OHIO STATE U
[5]   STUDIES OF AUSTRALIAN SOFT CORALS .43. THE STRUCTURE ELUCIDATION OF A NEW DITERPENE FROM ALCYONIUM-MOLLE [J].
BOWDEN, BF ;
COLL, JC ;
DAI, MC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (05) :665-673
[6]  
BRUCKNER C, 1988, J ORG CHEM, V53, P2450
[7]   DIASTEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED TETRAHYDROFURAN DERIVATIVES FROM GAMMA-LACTOLS [J].
BRUCKNER, C ;
LOREY, H ;
REISSIG, HU .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :556-557
[8]   THE CHEMISTRY AND CHEMICAL ECOLOGY OF OCTOCORALS (COELENTERATA, ANTHOZOA, OCTOCORALLIA) [J].
COLL, JC .
CHEMICAL REVIEWS, 1992, 92 (04) :613-631
[9]   ASYMMETRIC DIELS-ALDER REACTIONS WITH 5-MENTHYLOXY-2(5H)-FURANONE [J].
DEJONG, JC ;
VANBOLHUIS, F ;
FERINGA, BL .
TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1247-1262
[10]   ASYMMETRIC-SYNTHESIS OF DECALINES AND HEXAHYDROINDANES [J].
DEJONG, JC ;
JANSEN, JFGA ;
FERINGA, BL .
TETRAHEDRON LETTERS, 1990, 31 (21) :3047-3050