Concise Stereoselective Total Synthesis of (4R, 6R)-Lactone Moiety Analog of Mevinoline and Compactin

被引：3

作者：

Rao, D. Chandra ^{[1
]}

Reddy, D. Kumar ^{[1
]}

Chinnababu, B. ^{[1
]}

Shekhar, V. ^{[1
]}

Venkateswarlu, Y. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Nat Prod Lab, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 22期

关键词：

FeCl3; HMGCo A reductase inhibitor; S-CBS reduction; REDUCTASE INHIBITORS; DERIVATIVES; ML-236B;

D O I：

10.1080/00397911.2012.754470

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and highly efficient synthetic route has been developed for analogue of HMGCo A reductase inhibitor (1). The strategy utilizes S-Corey-Bakshi-Shibata (CBS) reduction, FeCl3-catalyzed C-H insertion of ethyl diazoacetate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource: Full experimental and spectral details.]

引用

页码：2980 / 2984

页数：5

共 50 条

[21] Stereoselective synthesis of (6R)- and (6S)-diosphenol and Ψ-diosphenol
Schneider, DF
Viljoen, MS
TETRAHEDRON, 2002, 58 (26) : 5307 - 5315
[22] A concise, stereoselective and scalable synthesis of optically pure (3R,4R)-1-benzyl- and (3R,4R)-1-Boc-3-methyl-4-aminopiperidines
Hazra, Sunit
Kangune, Ankit
Pawar, Govind
Karmakar, Ananta
Pabbisetty, Kumar B.
Mortensen, Deborah S.
Dodd, Dharmpal S.
Li, Jianqing
Mathur, Arvind
Gupta, Anuradha
Nimje, Roshan Y.
TETRAHEDRON, 2024, 167
[23] Stereoselective synthesis of methyl branched chiral deoxypropionate units: a new route for synthesis of insect pheromone (-)-lardolure and (2R,4R,6R,8R) 2,4,6,8-tetramethylundecanoic acid
Yadav, J. S.
Sengupta, Sandip
Yadav, Nagendra Nath
Chary, D. Narasimha
Al Ghamdi, Ahmad Alkhazim
TETRAHEDRON LETTERS, 2012, 53 (44) : 5952 - 5954
[24] Corrigendum to "First stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one" [Tetrahedron Lett. 48 (2007) 2013]
Krishna, Palakodety Radha
Srinivas, Ravula
TETRAHEDRON LETTERS, 2007, 48 (28) : 4951 - 4951
[25] Stereoselective synthesis of steroidal (6R)-spiro-1′,3′,4′-thiadiazolines
Shamsuzzaman
Aslam, M
Salim, A
JOURNAL OF CHEMICAL RESEARCH, 1998, (12) : 824 - 825
[26] Toward a scalable asymmetric synthesis of (4R,5S,6R) Trihydroxycyclohexen-2-one
Rosenberg, Ashley
McIntosh, Matt
Clay, David
Gibson, Andrew
Williams, David
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[27] Enantioselective synthesis and selective monofunctionalization of (4R,6R)-4,6-dihydroxy-2,8-dioxabicyclo[3.3.0]octane
Linclau, Bruno
Jeffery, Martin J.
Josse, Solen
Tomassi, Cyrille
ORGANIC LETTERS, 2006, 8 (25) : 5821 - 5824
[28] (2R,4R,6R,8R)-2,4,6,8-TETRAMETHYLDECANOIC AND (2R,4R,6R,8R)-2,4,6,8-UNDECANOIC ACID OF THE PREEN-GLAND WAX FROM THE DOMESTIC GOOSE, ANSER-A-F-DOMESTICUS - ISOLATION, SYNTHESIS OF DERIVATIVES AND OF THE RAC-2,4,6,8-TETRAMETHYLDECANOIC ACID
MORR, M
WRAY, V
FORTKAMP, J
SCHMID, RD
LIEBIGS ANNALEN DER CHEMIE, 1992, (05): : 433 - 439
[29] Enantioselective synthesis of the (5S, 6R, 9R) and (5S, 6R, 9S) analogs of lactacystin β-lactone
Corey, EJ
Li, WDZ
TETRAHEDRON LETTERS, 1998, 39 (44) : 8043 - 8046
[30] Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer
Reddy, D. Kumar
Shekhar, V.
Prabhakar, P.
Babu, B. Chinna
Siddhardha, B.
Murthy, U. S. N.
Venkateswarlu, Y.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (10) : 4657 - 4663

← 1 2 3 4 5 →