A NEW ROUTE TO CHIRAL PYRROLIDINES VIA RADICAL CYCLIZATION - ENANTIOSELECTIVE SYNTHESIS OF (+)-BULGECININE

被引:28
作者
YUASA, Y [1 ]
ANDO, J [1 ]
SHIBUYA, S [1 ]
机构
[1] TOKYO COLL PHARM, HACHIOJI, TOKYO 19203, JAPAN
关键词
D O I
10.1039/c39940001383
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reaction of the aldehyde 11 with tributyltin hydride in the presence of AIBN g
引用
收藏
页码:1383 / 1384
页数:2
相关论文
共 11 条
[1]   ELECTROCHEMICAL OXIDATION OF PROLINE DERIVATIVES - TOTAL SYNTHESES OF BULGECININE AND BULGECIN-C [J].
BARRETT, AGM ;
PILIPAUSKAS, D .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2787-2800
[2]   SYNTHESIS OF 2S,4S,5S-DIHYDROXYPIPECOLIC ACID AND BULGECININE [2S,4S,5R-4-HYDROXY-5-(HYDROXYMETHYL)PROLINE] FROM D-GLUCURONOLACTONE - A STRATEGY FOR THE SYNTHESIS OF 2S,4S-4-HYDROXY-ALPHA-AMINO ACIDS [J].
BASHYAL, BP ;
CHOW, HF ;
FLEET, GWJ .
TETRAHEDRON, 1987, 43 (02) :423-430
[3]   TRIBUTYLTIN HYDRIDE-INDUCED O-STANNYL KETYLS IN THE CYCLIZATION OF ALDEHYDES AND KETONES WITH ALKENES [J].
ENHOLM, EJ ;
PRASAD, G .
TETRAHEDRON LETTERS, 1989, 30 (37) :4939-4942
[4]   AN EFFICIENT SYNTHESIS OF (-)-BULGECININE [J].
HIRAI, Y ;
TERADA, T ;
AMEMIYA, Y ;
MOMOSE, T .
TETRAHEDRON LETTERS, 1992, 33 (51) :7893-7894
[5]   SHORT, STEREOSELECTIVE SYNTHESES OF 4,5,6-TRIHYDROXYLATED NORLEUCINES - AN APPROACH TO THE SYNTHESIS OF (+)-BULGECININE [J].
JACKSON, RFW ;
RETTIE, AB .
TETRAHEDRON LETTERS, 1993, 34 (18) :2985-2986
[6]   PHEROMONE SYNTHESIS .24. SYNTHESIS OF OPTICALLY-ACTIVE FORMS OF IPSDIENOL AND IPSENOL - PHEROMONE COMPONENTS OF IPS BARK BEETLES [J].
MORI, K ;
TAKIGAWA, T ;
MATSUO, T .
TETRAHEDRON, 1979, 35 (08) :933-940
[7]   STEREOSELECTIVE HYDROXYLATION OF N-CARBAMOYL-L-PYROGLUTAMATE - SYNTHESIS OF (-)-BULGECININE [J].
OHTA, T ;
HOSOI, A ;
NOZOE, S .
TETRAHEDRON LETTERS, 1988, 29 (03) :329-332
[8]   STRUCTURES OF BULGECINS, BACTERIAL METABOLITES WITH BULGE-INDUCING ACTIVITY [J].
SHINAGAWA, S ;
KASAHARA, F ;
WADA, Y ;
HARADA, S ;
ASAI, M .
TETRAHEDRON, 1984, 40 (18) :3465-3470
[9]   A NOVEL STEREOSPECIFIC RADICAL CYCLIZATION OF 2',3'-O-ISOPROPYLIDENEURIDINE AND 2',3'-O-ISOPROPYLIDENE-ADENOSINE 5'-ALDEHYDE TO THE CORRESPONDING 6,5'-CYCLODIHYDROURIDINE AND 8,5'-CYCLOADENOSINE DERIVATIVES [J].
SUGAWARA, T ;
OTTER, BA ;
UEDA, T .
TETRAHEDRON LETTERS, 1988, 29 (01) :75-78
[10]   BLOOD-GROUP LI-ACTIVE OLIGOSACCHARIDES - SYNTHESIS OF A TETRASACCHARIDE, A BETA-(1-]3) DIMER OF N-ACETYL-LACTOSAMINE [J].
VEYRIERES, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1626-1629