Synthesis of the antifungal macrolide antibiotic (+)-roxaticin

被引：85

作者：

Evans, DA ^{[1
]}

Connell, BT ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 36期

关键词：

D O I：

10.1021/ja027638q

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of the antifungal macrolide antibiotic roxaticin has been accomplished. The synthesis relies principally on aldol and directed reduction steps to construct the extended 1,3-polyol array present in the natural product. Three principal nonpolyene containing fragments were assembled and then coupled using Julia olefination and methyl ketone aldol addition reactions. A series of functionalization reactions incorporated the sensitive polyene and provided the protected roxaticin seco-acid, which was lactonized in good yield. Acidic deprotection completed this convergent synthesis of roxaticin.

引用

页码：10899 / 10905

页数：7

共 63 条

[21] 1,5-asymmetric induction in methyl ketone aldol addition reactions
Evans, DA
Coleman, PJ
Cote, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) : 788 - 789
[22] Enantioselective total synthesis of altohyrtin C (spongistatin 2)
Evans, DA
Trotter, BW
Coleman, PJ
Côté, B
Dias, LC
Rajapakse, HA
Tyler, AN
[J]. TETRAHEDRON, 1999, 55 (29) : 8671 - 8726
[23] C2-symmetric copper(II) complexes as chiral Lewis acids.: Scope and mechanism of catalytic enantioselective aldol additions of enolsilanes to (benzyloxy)acetaldehyde
Evans, DA
Kozlowski, MC
Murry, JA
Burgey, CS
Campos, KR
Connell, BT
Staples, RJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) : 669 - 685
[24] ALKYLLITHIUM REAGENTS FROM ALKYL-HALIDES AND LITHIUM RADICAL-ANIONS
FREEMAN, PK
HUTCHINSON, LL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) : 1924 - 1930
[25] GAGE JR, 1989, ORG SYNTH, V66, P83
[26] NUCLEOTIDES .4. CONVERSION OF RIBONUCLEOSIDES TO NEW 2',3'-KETAL DERIVATIVES
HAMPTON, A
FRATANTONI, JC
CARROLL, PM
WANG, SC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (23) : 5481 - +
[27] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS
HORITA, K
YOSHIOKA, T
TANAKA, T
OIKAWA, Y
YONEMITSU, O
[J]. TETRAHEDRON, 1986, 42 (11) : 3021 - 3028
[28] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION
INANAGA, J
HIRATA, K
SAEKI, H
KATSUKI, T
YAMAGUCHI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) : 1989 - 1993
[29] 3-ACYLTETRAMIC ACID ANTIBIOTICS .2. SYNTHESIS OF (+)-STREPTOLIC ACID
IRELAND, RE
SMITH, MG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (03) : 854 - 860
[30] REGIOSELECTIVE REDUCTIVE RING-OPENING OF 4-METHOXYBENZYLIDENE ACETALS OF HEXOPYRANOSIDES - ACCESS TO A NOVEL PROTECTIVE GROUP STRATEGY
JOHANSSON, R
SAMUELSSON, B
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) : 201 - 202

← 1 2 3 4 5 6 7 →