A ROUTE FOR THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF ANTHERIDIC ACID, THE ANTHERIDIUM-INDUCING FACTOR FROM ANEMIA-PHYLLITIDIS

被引：34

作者：

COREY, EJ

KIGOSHI, H

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 38期

关键词：

D O I：

10.1016/S0040-4039(00)93418-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An effective route for the total synthesis of antheridic acid (1) has been devised in which the initial chiral intermediate 7 is generated by enantioselective catalytic reduction and transformed in a stereocontrolled fashion into key intermediates 9, 10, 13, and 2.

引用

收藏

页码：5025 / 5028

页数：4

相关论文

共 16 条

[1] AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].

COREY, EJ ;

SHIBATA, S ;

BAKSHI, RK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863

[2] A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION [J].

COREY, EJ ;

LINK, JO .

TETRAHEDRON LETTERS, 1989, 30 (46) :6275-6278

[3] A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].

COREY, EJ ;

BAKSHI, RK .

TETRAHEDRON LETTERS, 1990, 31 (05) :611-614

[4] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553

[5] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES [J].

COREY, EJ ;

BAKSHI, RK ;

SHIBATA, S ;

CHEN, CP ;

SINGH, VK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926

[6] TOTAL SYNTHESIS OF (+/-)-ANTHERIDIUM-INDUCING FACTOR (AAN,2) OF THE FERN ANEMIA PHYLLITIDIS - CLARIFICATION OF STEREOCHEMISTRY [J].

COREY, EJ ;

MYERS, AG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5574-5576

[7] CONSTITUTION OF ANTHERIDIUM-INDUCING FACTOR OF ANEMIA-PHYLLITIDIS [J].

COREY, EJ ;

MYERS, AG ;

TAKAHASHI, N ;

YAMANE, H ;

SCHRAUDOLF, H .

TETRAHEDRON LETTERS, 1986, 27 (42) :5083-5084

[8] NEW ENANTIOSELECTIVE ROUTES TO BIOLOGICALLY INTERESTING COMPOUNDS [J].

COREY, EJ .

PURE AND APPLIED CHEMISTRY, 1990, 62 (07) :1209-1216

[9]

COREY EJ, 1989, 31ST P NAT ORG S, P1

[10] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519