The stereoselective total synthesis of PF1163A

被引：10

作者：

Kumar, Harish ^{[1
]}

Reddy, A. Srinivas ^{[1
]}

Reddy, B. V. Subba ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 09期

关键词：

Antifungal agent; Evans methylation; Yamaguchi esterification; Ring closing metathesis; ANTIFUNGAL AGENT; DERIVATIVES; ALCOHOLS;

D O I：

10.1016/j.tetlet.2014.01.031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective total synthesis of 13-membered macrocycle PF1163A, an antifungal agent, has been accomplished for the first time starting from D-xylose. This approach involves a diastereoselective allylation of lactal ether,(3a) reductive ring opening of tetrahydrofuran ring,(3b) asymmetric methylation reaction, Yamaguchi esterification, and ring closing metathesis as key steps. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：1519 / 1522

页数：4

共 18 条

[1] Total synthesis and conformational analysis of the antifungal agent (-)-PF1163B [J].

Bouazza, F ;

Renoux, B ;

Bachmann, C ;

Gesson, JP .

ORGANIC LETTERS, 2003, 5 (22) :4049-4052

[2] Synthetic studies toward potent cytotoxic agents amphidinolides G and H:: Synthesis of the entire C15-C26 moiety of the top half [J].

Chakraborty, TK ;

Suresh, VR .

TETRAHEDRON LETTERS, 1998, 39 (42) :7775-7778

[3] ASYMMETRIC ALKYLATION REACTIONS OF CHIRAL IMIDE ENOLATES - A PRACTICAL APPROACH TO THE ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED CARBOXYLIC-ACID DERIVATIVES [J].

EVANS, DA ;

ENNIS, MD ;

MATHRE, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (06) :1737-1739

[4] RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].

INANAGA, J ;

HIRATA, K ;

SAEKI, H ;

KATSUKI, T ;

YAMAGUCHI, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993

[5] A stereoelectronic model to explain the highly stereoselective reactions of nucleophiles with five-membered-ring oxocarbenium ions [J].

Larsen, CH ;

Ridgway, BH ;

Shaw, JT ;

Woerpel, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (51) :12208-12209

[6] On the Selective N-Methylation of BOC-Protected Amino Acids [J].

Malkov, Andrei V. ;

Vrankova, Kvetoslava ;

Cerny, Miloslav ;

Kocovsky, Pavel .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8425-8427

[7] PF1163A, a novel antifungal agent, inhibit ergosterol biosynthesis at C-4 sterol methyl oxidase [J].

Nose, H ;

Fushimi, H ;

Seki, A ;

Sasaki, T ;

Watabe, H ;

Hoshiko, S .

JOURNAL OF ANTIBIOTICS, 2002, 55 (11) :969-974

[8] PF1163A and B, new antifungal antibiotics produced by Penicillium sp I.: Taxonomy of producing strain, fermentation, isolation and biological activities [J].

Nose, H ;

Seki, A ;

Yaguchi, T ;

Hosoya, A ;

Sasaki, T ;

Hoshiko, S ;

Shomura, T .

JOURNAL OF ANTIBIOTICS, 2000, 53 (01) :33-37

[9] THE RING-OPENING METATHESIS POLYMERIZATION OF 7-OXABICYCLO[2.2.1]HEPT-5-ENE DERIVATIVES - A NEW ACYCLIC POLYMERIC IONOPHORE [J].

NOVAK, BM ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (03) :960-961

[10] OXIDATION OF ALCOHOLS BY ACTIVATED DIMETHYL-SULFOXIDE - PREPARATIVE, STERIC AND MECHANISTIC STUDY [J].

OMURA, K ;

SWERN, D .

TETRAHEDRON, 1978, 34 (11) :1651-1660

← 1 2 →