Enantioselective synthesis of (-)-cis-clavicipitic acid

被引:46
作者
Ku, Jin-Mo
Jeong, Byeong-Seon
Jew, Sang-sup [1 ]
Park, Hyeung-geun
机构
[1] Seoul Natl Univ, Res Inst Pharmaceut Sci, Seoul 151742, South Korea
[2] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
[3] Yeungnam Univ, Coll Pharm, Kyongsan 712749, South Korea
关键词
D O I
10.1021/jo071162h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] An enantioselective synthetic method for (-)-cis-clavicipitic acid (1) was reported. 1 was obtained in 10 steps (99% ee and 20% overall yield) from 1H-indole-3-carboxylic acid methyl ester (9) via asymmetric phase-transfer catalytic alkylation and diastereoselective Pd(II)-catalyzed intramolecular aminocyclization as key steps.
引用
收藏
页码:8115 / 8118
页数:4
相关论文
共 30 条
[1]   FORMATION OF CLAVICIPITIC ACID IN CELL-FREE SYSTEMS OF CLAVICEPS SP [J].
BAJWA, RS ;
KOHLER, RD ;
SAINI, MS ;
CHENG, M ;
ANDERSON, JA .
PHYTOCHEMISTRY, 1975, 14 (03) :735-737
[2]   FORMAL SYNTHESIS OF CLAVICIPITIC ACID BASED ON A BIOSYNTHETIC PROPOSAL [J].
BOYLES, DA ;
NICHOLS, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5128-5130
[3]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[4]   PALLADIUM-CATALYZED REACTIONS IN THE SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED INDOLES .2. TOTAL SYNTHESIS OF THE N-ACETYL METHYL-ESTER OF (+/-)-CLAVICIPITIC ACIDS [J].
HARRINGTON, PJ ;
HEGEDUS, LS ;
MCDANIEL, KF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (14) :4335-4338
[5]   AN EFFICIENT SYNTHESIS OF (-)-BULGECININE [J].
HIRAI, Y ;
TERADA, T ;
AMEMIYA, Y ;
MOMOSE, T .
TETRAHEDRON LETTERS, 1992, 33 (51) :7893-7894
[6]   A concise total synthesis of (+/-)-cis- and (+/-)-trans-clavicipitic acids by combinational use of directed lithiation and fluoride ion-induced elimination-addition reaction of 1-(triisopropylsilyl)gramine derivatives [J].
Iwao, M ;
Ishibashi, F .
TETRAHEDRON, 1997, 53 (01) :51-58
[7]   Highly enantioselective synthesis of α-alkyl-alanines via the catalytic phase-transfer alkylation of 2-naphthyl aldimine tert-butyl ester by using O(9)-allyl-N(1)-2′,3′,4′-trifluorobenzylhydro-cinchonidinium bromide [J].
Jew, SS ;
Jeong, BS ;
Lee, JH ;
Yoo, MS ;
Lee, YJ ;
Park, BS ;
Kim, MG ;
Park, HG .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4514-4516
[8]   Synthesis and application of dimeric Cinchona alkaloid phase-transfer catalysts:: α,α′-bis[O(9)-allylcinchonidinium]-o, m, or p-xylene dibromide [J].
Jew, SS ;
Jeong, BS ;
Yoo, MS ;
Huh, H ;
Park, HG .
CHEMICAL COMMUNICATIONS, 2001, (14) :1244-1245
[9]   Selective tert-butyl ester deprotection in the presence of acid labile protecting groups with use of ZnBr2 [J].
Kaul, R ;
Brouillette, Y ;
Sajjadi, Z ;
Hansford, KA ;
Lubell, WD .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :6131-6133
[10]   First asymmetric total synthesis of (-)-antofine by using an enantioselective catalytic phase transfer alkylation [J].
Kim, S ;
Lee, J ;
Lee, T ;
Park, HG ;
Kim, D .
ORGANIC LETTERS, 2003, 5 (15) :2703-2706