Enantioselective Synthesis of Nabscessin C

被引：1

作者：

Yeh, Chun-Wei ^{[1
]}

Feng, Chia-Chi ^{[1
]}

Chen, Pei-Lin ^{[2
]}

Jhou, Yi-Jhen ^{[1
]}

Hou, Duen-Ren ^{[1
]}

机构：

[1] Natl Cent Univ, Dept Chem, Taoyuan 32001, Taiwan

[2] Natl Tsing Hua Univ, Instrument Ctr, Hsinchu 300044, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 19期

关键词：

ALPHA-GLUCOSIDASE INHIBITORS; AMINOGLYCOSIDE ANTIBIOTICS; CHEMOENZYMATIC SYNTHESIS; BIOSYNTHETIC-PATHWAY; CONVENIENT SYNTHESIS; DERIVATIVES; INOSITOL; DESYMMETRIZATION; INOSAMYCIN; COMPLEX;

D O I：

10.1021/acs.joc.3c01064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective synthesis of nabscessin C (1), an aminocyclitol amide with antimicrobial activity, is reported. Starting from myo-inositol, (+)-nabscessin C was synthesized in 12 isolation steps. Desymmetrization of 2-deoxygenated 4,6-dibenzylinositol was achieved using lipase from porcine pancreas (PPL), and the stereochemistry was established by X-ray crystallography. This method has the potential for synthesizing other cyclitol-derived compounds.

引用

收藏

页码：13528 / 13534

页数：7

相关论文

共 42 条

[1] THE INVENTION OF RADICAL REACTIONS .32. RADICAL DEOXYGENATIONS, DEHALOGENATIONS, AND DEAMINATIONS WITH DIALKYL PHOSPHITES AND HYPOPHOSPHOROUS ACID AS HYDROGEN SOURCES [J].

BARTON, DHR ;

JANG, DO ;

JASZBERENYI, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6838-6842

[2] NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].

BARTON, DHR ;

MCCOMBIE, SW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585

[3] THE TOTAL SYNTHESIS OF MYOINOSITOL PHOSPHATES VIA MYOINOSITOL ORTHOFORMATE [J].

BILLINGTON, DC ;

BAKER, R ;

KULAGOWSKI, JJ ;

MAWER, IM ;

VACCA, JP ;

DESOLMS, SJ ;

HUFF, JR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (08) :1423-1429

[4] Aminoglycosides: Time for the Resurrection of a Neglected Class of Antibacterials? [J].

Boettger, Erik C. ;

Crich, David .

ACS INFECTIOUS DISEASES, 2020, 6 (02) :168-+

[5] Antifungal amphiphilic aminoglycosides [J].

Chang, C. -W. T. ;

Takemoto, Y. .

MEDCHEMCOMM, 2014, 5 (08) :1048-1057

[6] Chemoenzymatic Synthesis of Inositols, Conduritols, and Cyclitol Analogues [J].

Duchek, Jan ;

Adams, David R. ;

Hudlicky, Tomas .

CHEMICAL REVIEWS, 2011, 111 (07) :4223-4258

[7] The aminoglycosides [J].

Edson, RS ;

Terrell, CL .

MAYO CLINIC PROCEEDINGS, 1999, 74 (05) :519-528

[8]

Fiori KW, 2009, NAT CHEM, V1, P630, DOI [10.1038/NCHEM.410, 10.1038/nchem.410]

[9] Isolation of Nabscessin C from Nocardia abscessus IFM 10029T and a Study on Biosynthetic Pathway for Nabscessins [J].

Hara, Shoko ;

Hara, Yasumasa ;

Arai, Midori A. ;

Kusuya, Yoko ;

Takahashi, Hiroki ;

Yaguchi, Takashi ;

Ishibashi, Masami .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2018, 66 (10) :976-982

[10] Nabscessins A and B, Aminocyclitol Derivatives from Nocardia abscessus IFM 10029T [J].

Hara, Shoko ;

Ishikawa, Naoki ;

Hara, Yasumasa ;

Nehira, Tatsuo ;

Sakai, Kanae ;

Gonoi, Tohru ;

Ishibashi, Masami .

JOURNAL OF NATURAL PRODUCTS, 2017, 80 (02) :565-568

← 1 2 3 4 5 →