Organocatalytic asymmetric syntheses of inthomycins A, B and C

被引：33

作者：

Yoshino, Madoka ^{[1
]}

Eto, Kohei ^{[1
]}

Takahashi, Keisuke ^{[1
]}

Ishihara, Jun ^{[1
]}

Hatakeyama, Susumi ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 40期

关键词：

MULTICOMPONENT COUPLING STRATEGY; CELLULOSE BIOSYNTHESIS; ALDOL REACTIONS; BETA-LACTONES; TRIENE COMPONENT; MICROBIAL ORIGIN; PHTHOXAZOLIN-A; OXAZOLOMYCIN; INHIBITOR; METABOLITES;

D O I：

10.1039/c2ob26084k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total syntheses of (+)-inthomycin A, (+)-inthomycin B and (-)-inthomycin C, the oxazole-triene antibiotics isolated from Streptomyces sp., have been accomplished via the highly enantio- and stereoselective construction of the C1-C7 (iododienyl)aldol units by taking advantage of a Cinchona alkaloid-catalyzed asymmetric P-lactone synthesis and their isomerisation-free Stille coupling with (E)-5-(3-(tributylstannyl)allyl)oxazole.

引用

页码：8164 / 8174

页数：11

共 50 条

[1] Andrews MD, 1996, SYNLETT, P612
[2] On the antibiotic activity of oxazolomycin
Bagwell, Claire L.
Moloney, Mark G.
Thompson, Amber L.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (14) : 4081 - 4086
[3] Oxazolomycins: Natural product lead structures for novel antibacterials by click fragment conjugation
Bagwell, Claire L.
Moloney, Mark G.
Yaqoob, Muhammad
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (07) : 2090 - 2094
[4] A synthesis of a common intermediate to the lactone pyrrolidinone ring systems in oxazolomycin A and neooxazolomycin
Bennett, Nicholas J.
Prodger, Jeremy C.
Pattenden, Gerald
[J]. TETRAHEDRON, 2007, 63 (27) : 6216 - 6231
[5] Radical hydrostannylation, Pd(0)-catalyzed hydrostannylation, stannylcupration of propargyl alcohols and enynols: Regio- and stereoselectivities
Betzer, JF
Delaloge, F
Muller, B
Pancrazi, A
Prunet, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7768 - 7780
[6] A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics
Bulger, PG
Moloney, MG
Trippier, PC
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (21) : 3726 - 3737
[7] Bulger PG, 2002, SYNLETT, P1871
[8] Intramolecular, nucleophile-catalyzed aldol-lactonization (NCAL) reactions:: Catalytic, asymmetric synthesis of bicyclic β-lactones
Cortez, GS
Tennyson, RL
Romo, D
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) : 7945 - 7946
[9] The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes:: Synthesis of (E)-1-tributylstannyl-1-alkenes
Darwish, Alla
Lang, Adam
Kim, Thomas
Chong, J. Michael
[J]. ORGANIC LETTERS, 2008, 10 (05) : 861 - 864
[10] Intramolecular hydrosilylation and silicon-assisted cross-coupling: An efficient route to trisubstituted homoallylic alcohols
Denmark, SE
Pan, WT
[J]. ORGANIC LETTERS, 2001, 3 (01) : 61 - 64

← 1 2 3 4 5 →