Formation of Substituted Tetrahydropyrans through Oxetane Ring Opening: Application to the Synthesis of C1-C17 Fragment of Salinomycin

被引：38

作者：

Yadav, J. S. ^{[1
,2
]}

Singh, Vinay K. ^{[1
,2
]}

Srihari, P. ^{[2
]}

机构：

[1] CSIR Indian Inst Chem Technol, Acad Sci & Innovat Res, Hyderabad 500007, Andhra Pradesh, India

[2] CSIR Indian Inst Chem Technol, Div Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 03期

关键词：

POLYETHER ANTIBIOTIC SALINOMYCIN; STEREOCONTROLLED TOTAL-SYNTHESIS; ASYMMETRIC ALDOL ADDITIONS; N-ACYL OXAZOLIDINONES; NATURAL-PRODUCTS; CHIRAL SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SEX-PHEROMONE; OXAZOLIDINETHIONES; CONVERGENT;

D O I：

10.1021/ol403604u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of C1-C17 fragment of salinomycin is achieved. The strategy employs a desymmetrization approach and utilizes an intramolecular oxetane opening reaction with O-nucleophile to result in the tetrahydropyran skeleton as the key step.

引用

页码：836 / 839

页数：4

共 61 条

[41] COMPARISONS OF RATE CONSTANTS FOR THIOLATE-DISULFIDE INTERCHANGE IN WATER AND IN POLAR APROTIC-SOLVENTS USING DYNAMIC H-1-NMR LINE-SHAPE ANALYSIS
SINGH, R
WHITESIDES, GM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) : 1190 - 1197
[42] Highly stereoselective aldol reaction based on titanium enolates from (S)-1-benzyloxy-2-methyl-3-pentanone
Solsona, JG
Nebot, J
Romea, P
Urpí, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (16) : 6533 - 6536
[43] STEREOCONTROLLED SYNTHESIS OF THE (+/-) DJERASSI-PRELOG LACTONIC ACID
STORK, G
NAIR, V
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (05) : 1315 - 1316
[44] TINO JA, 1987, HETEROCYCLES, V25, P97
[45] Total synthesis of (+)-amphidinolide A. Assembly of the fragments
Trost, BM
Wrobleski, ST
Chisholm, JD
Harrington, PE
Jung, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (39) : 13589 - 13597
[46] LIPASE-CATALYZED ASYMMETRIC-SYNTHESIS OF CHIRAL 1,3-PROPANEDIOLS AND ITS APPLICATION TO THE PREPARATION OF OPTICALLY PURE BUILDING BLOCK FOR RENIN INHIBITORS
TSUJI, K
TERAO, Y
ACHIWA, K
[J]. TETRAHEDRON LETTERS, 1989, 30 (45) : 6189 - 6192
[47] NUCLEOPHILIC OPENING OF OXETANE RINGS IN 3,5-ANHYDRO-1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE AND -ALPHA-D-XYLOFURANOSE
WHISTLER, RL
LUTTENEG.TJ
ROWELL, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) : 396 - &
[48] Saliniketals A and B, bicyclic polyketides from the marine actinomycete Salinispora arenicola
Williams, Philip G.
Asolkar, Ratnakar N.
Kondratyuk, Tamara
Pezzuto, John M.
Jensen, Paul R.
Fenical, William
[J]. JOURNAL OF NATURAL PRODUCTS, 2007, 70 (01): : 83 - 88
[49] Synthesis and biological evaluation of isonucleosides derived from methyl 3,5-anhydro-2-O-(2-fluorobenzyl)- D-xylofuranosides
Wirsching, J
Schulze, O
Voss, J
Giesler, A
Kopf, J
Adiwidjaja, G
Balzarini, J
De Clercq, E
[J]. NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2002, 21 (03) : 257 - 274
[50] PERIODATE OXIDATION OF CYCLIC 1,3-DIKETONES
WOLFROM, ML
BOBBITT, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (11) : 2489 - 2493

← 1 2 3 4 5 6 7 →