Total Synthesis of (+)-Brefeldin C, (+)-nor-Me Brefeldin A and (+)-4-epi-nor-Me Brefeldin A

被引：21

作者：

Archambaud, Sylvie ^{[1
]}

Legrand, Frederic ^{[1
]}

Aphecetche-Julienne, Karine ^{[1
]}

Collet, Sylvain ^{[1
]}

Guingant, Andre ^{[1
]}

Evain, M. ^{[2
]}

机构：

[1] Univ Nantes, CNRS, UMR 6230, F-44322 Nantes 3, France

[2] Inst Mat Jean Rouxel, F-44322 Nantes 03, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 07期

关键词：

G protein; Brefeldin A analogues; Desymmetrization; Macrolactonization; Macrocycles; Asymmetric synthesis; Total synthesis; MACROLIDE ANTIBIOTICS; ASYMMETRIC-SYNTHESIS; GUANINE-NUCLEOTIDE; ENANTIOSELECTIVE SYNTHESIS; CYCLIC ANHYDRIDES; DIRECT ADDITION; BIOSYNTHESIS; EXCHANGE; ALDEHYDES; DECUMBIN;

D O I：

10.1002/ejoc.200901233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed, Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the absolute configuration at C4 of BFC, a Suzuki-Miyaura cross-coupling reaction to create the C11-C12 bond and a Yamaguchi reaction to form the 13-membered lactone ring.

引用

页码：1364 / 1380

页数：17

共 74 条

[1] PENICILLIUM-CAMEMBERTI A NEW SOURCE OF BREFELDIN-A [J].

ABRAHAM, WR ;

ARFMANN, HA .

PLANTA MEDICA, 1992, 58 (05) :484-484

[2] A new total synthesis of (+)-brefeldin C [J].

Archambaud, S ;

Aphecetche-Julienne, K ;

Guingant, A .

SYNLETT, 2005, (01) :139-143

[3] Asymmetric synthesis of chiral bisoxazolines and their use as ligands in metal catalysis [J].

Atodiresei, I ;

Schiffers, I ;

Bolm, C .

TETRAHEDRON-ASYMMETRY, 2006, 17 (04) :620-633

[4] Stereoselective anhydride openings [J].

Atodiresei, Luliana ;

Schiffers, Ingo ;

Bolm, Carsten .

CHEMICAL REVIEWS, 2007, 107 (12) :5683-5712

[5]

BALLINI R, 2002, SYNTHESIS-STUTTGART, V5, P681

[6] BIOLOGICAL EFFECTS OF THE ANTIBIOTIC BREFELDIN-A (DECUMBIN, CYANEIN, ASCOTOXIN, SYNERGISIDIN) - A RETROSPECTIVE [J].

BETINA, V .

FOLIA MICROBIOLOGICA, 1992, 37 (01) :3-11

[7] CYANEIN, A NEW ANTIBIOTIC FROM PENICILLIUM-CYANEUM [J].

BETINA, V ;

BARATH, Z ;

NEMEC, P ;

DOBIAS, J .

FOLIA BIOLOGICA, 1962, 7 (06) :353-&

[8] Practical and highly enantioselective ring opening of cyclic meso-anhydrides mediated by cinchona alkaloids [J].

Bolm, C ;

Schiffers, I ;

Dinter, CL ;

Gerlach, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (21) :6984-6991

[9]

Bolm C, 1999, SYNLETT, P195

[10]

Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO

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