Enantioselective synthesis of the tetracyclic left-hand substructure of solanoeclepin A

被引:27
作者
Benningshof, JCJ
Blaauw, RH
van Ginkel, AE
Rutjes, FPJT
Fraanje, J
Goubitz, K
Schenk, H
Hiemstra, H
机构
[1] Univ Amsterdam, Organ Chem Lab, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands
[2] Univ Amsterdam, Crystallog Lab, Inst Mol Chem, NL-1018 WS Amsterdam, Netherlands
关键词
D O I
10.1039/b003757p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of the enantiopure left-hand substructure of solanoeclepin A is described. Key steps include a chromium-mediated coupling of an oxabicyclic aldehyde with a beta-ketoester-derived enol triflate to give a lactone, and a ring-closing metathesis reaction to form the seven-membered ring.
引用
收藏
页码:1465 / 1466
页数:2
相关论文
共 16 条
[1]   Intramolecular [2+2] photocycloadditions as an approach towards the bicyclo[2.1.1]hexane substructure of solanoeclepin A [J].
Blaauw, RH ;
Brière, JF ;
de Jong, R ;
Benningshof, JCJ ;
van Ginkel, AE ;
Rutjes, FPJT ;
Fraanje, J ;
Goubitz, K ;
Schenk, H ;
Hiemstra, H .
CHEMICAL COMMUNICATIONS, 2000, (16) :1463-1464
[2]   HYDROBORATION .45. NEW, CONVENIENT PREPARATIONS OF REPRESENTATIVE BORANE REAGENTS UTILIZING BORANE-METHYL SULFIDE [J].
BROWN, HC ;
MANDAL, AK ;
KULKARNI, SU .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (08) :1392-1398
[3]   READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156
[4]   Chemoselective debenzylation involving removal of a 2-hydroxy-1-phenylethyl group from nitrogen [J].
Fains, O ;
Vernon, JM .
TETRAHEDRON LETTERS, 1997, 38 (47) :8265-8266
[5]   CAROTENOIDS WITH 7-OXABICYCLO[2.2.1]HEPTYL END GROUPS .2. SYNTHESIS OF (2S,5R,6S,2'S,5'R,6'S)-2,5-2',5'-DIEPOXY-5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE [J].
GMUNDER, MR ;
EUGSTER, CH .
HELVETICA CHIMICA ACTA, 1990, 73 (08) :2190-2198
[6]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[7]   Enantioselective total synthesis of aspidophytine [J].
He, F ;
Bo, YX ;
Altom, JD ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6771-6772
[8]   IMPROVED PROCEDURE FOR DIRECT OXIDATION OF OLEFINS TO ALPHA-DIKETONES BY POTASSIUM PERMANGANATE IN ACETIC-ANHYDRIDE [J].
JENSEN, HP ;
SHARPLES.KB .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (15) :2314-2314
[9]   PREPARATION AND REACTIVITY OF FUNCTIONALIZED ALKENYL-ZINC, ALKENYL-COPPER, AND ALKENYL-CHROMIUM ORGANOMETALLICS [J].
KNOCHEL, P ;
RAO, CJ .
TETRAHEDRON, 1993, 49 (01) :29-48
[10]  
LEY SV, 1994, SYNTHESIS-STUTTGART, P639