Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam.

被引：23

作者：

Oppolzer, W ^{[1
]}

Walther, E ^{[1
]}

Balado, CP ^{[1
]}

DeBrabander, J ^{[1
]}

机构：

[1] UNIV GENEVA,DEPT CHIM ORGAN,CH-1211 GENEVA,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(96)02408-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from N-propionylbornanesultam ent-a yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 --> 7) followed by saponification of the sultam moiety (7 --> 4) provided the Prelog-Djerassi lactonic acid 4 in a three step sequence in 61-71% overall yield. (C) 1997, Elsevier Science Ltd.

引用

页码：809 / 812

页数：4

共 34 条

[1] STUDIES TOWARDS THE TOTAL SYNTHESIS OF RAPAMYCIN - A CONVERGENT AND STEREOSELECTIVE SYNTHESIS OF THE C22-C32 CARBON FRAMEWORK
ANDERSON, JC
LEY, SV
MARSDEN, SP
[J]. TETRAHEDRON LETTERS, 1994, 35 (13) : 2087 - 2090
[2] STOFFWECHSELPRODUKTE VON ACTINOMYCETEN .5. UBER DAS LACTON DER BETA-HYDROXY-ALPHA, ALPHA', GAMMA-TRIMETHYL-PIMELINSAURE, EIN ABBAUPRODUKT VON NARBOMYCIN, PIKROMYCIN UND METHYMYCIN
ANLIKER, R
DVORNIK, D
GUBLER, K
HEUSSER, H
PRELOG, V
[J]. HELVETICA CHIMICA ACTA, 1956, 39 (06) : 1785 - 1790
[3] [Anonymous], [No title captured]
[4] THE STRUCTURE OF THE ANTIBIOTIC METHYMYCIN
DJERASSI, C
ZDERIC, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (24) : 6390 - 6395
[5] TOTAL SYNTHESIS OF THE MACROLIDE ANTIBIOTIC RUTAMYCIN-B
EVANS, DA
NG, HP
RIEGER, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) : 11446 - 11459
[6] DOUBLE STEREODIFFERENTIATING ALDOL REACTIONS - THE DOCUMENTATION OF PARTIALLY MATCHED ALDOL BOND CONSTRUCTIONS IN THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS
EVANS, DA
DART, MJ
DUFFY, JL
RIEGER, DL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) : 9073 - 9074
[7] STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES
EVANS, DA
NELSON, JV
VOGEL, E
TABER, TR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) : 3099 - 3111
[8] TOTAL SYNTHESIS OF THE POLYETHER ANTIBIOTIC LONOMYCIN-A (EMERICID)
EVANS, DA
RATZ, AM
HUFF, BE
SHEPPARD, GS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) : 3448 - 3467
[9] STEREOSELECTIVE REACTIONS OF CHIRAL ENOLATES - APPLICATION TO THE SYNTHESIS OF (+)-PRELOG-DJERASSI LACTONIC ACID
EVANS, DA
BARTROLI, J
[J]. TETRAHEDRON LETTERS, 1982, 23 (08) : 807 - 810
[10] FRANKLIN AS, 1994, CONTEMP ORG SYNTH, P317

← 1 2 3 4 →