Enantioselective reduction of meso-cyclic-1,2-dicarboxylic anhydrides and 1,2-dicarboximides: Asymmetric synthesis of bicyclic lactones and hydroxylactams

DOI: 10.1248/cpb.42.9

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 9 - 18 (1994)

Update date:2022-08-05

Topics:

Authors:

Matsuki Matsuki

Inoue Inoue

Ishida Ishida

Takeda Takeda

Nakagawa

Hino Hino

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1248/cpb.42.9

Chiral bicyclic lactones (3,8,9) and bicyclic hydroxylactams (10-13) were synthesized by highly enantioselective reduction of meso-cyclic-1,2- dicarboxylic anhydrides (1, 4) and meso-cyclic-1,2-dicarboximides (2) with lithium aluminum hydride (LiAlH₄)-alcohol(ROH)-(R)- or (S)-1,1'-bi-2- naphthol complex [(R)- or (S)-BINAL-H(ROH)]. Treatment of the hydroxylactams (10-13) with triethylsilane (Et₃SiH) and trifluoroacetic acid (CF₃CO₂H) gave chiral bicyclic lactams (14, 15) in quantitative yields. Removal of the N-4-methoxyphenyl group of the lactams (14, 15) with cerium(IV) ammonium nitrate (CAN) proceeded smoothly to give the corresponding N-unsubstituted lactams (16, 17) in high optical purity.

Full text of DOI:10.1248/cpb.42.9

NII-Electronic Library Service

Products guided by the article

Product name:(3S,3aS,4S,7R,7aR)-2,3,3a,4,7,7a-hexahydro-3-hydroxy-4,7-methano-2-(4-methoxyphenyl)-1H-isoindol-1-one

Cas No:158999-72-5

R&D Labs maybe for 158999-72-5

Jiangxi Hessence Chemicals Co., Ltd.

Contact:+86 796 3511924

Address:Chengxi Industrial Park, Jishui County, Jiangxi Province 331600 China.
Shanghai Coupling Pharmaceutical R&D Co., Ltd.(expird)

Contact:+86 021 50106671

Address:403 Room No.4 Buiding, No. 526 Ruiqing Road, Shanghai Zhangjiang Hi-Tech Park
Shanghai Dano Pharmaceutical Co.,Ld.(expird)

Contact:+86-592-6266840

Address:Building 1 Room 512, 720 Cailun Rd, Zhangjiang High-Tech Park, Shanghai 201203, China
Hefei Highzone Fine Chemical S&T CO.,LTD

Contact:86-0551-63663560

Address:room 1801 NO. 24 Shuguang RD.
Changsha Botaniex Inc.

Contact:(86) 731 88718666

Address:Room 1222, Unit 4, Building B, Shangcheng, No.47, Kaiyuan East Road.

Relevant to this article

Chiral smectic *C mesogens having ester and amide central linkages

Doi:10.1080/15421400801915027
(2008)
Microwave-assisted parallel synthesis of benzofuran-2-carboxamide derivatives bearing anti-inflammatory, analgesic and antipyretic agents

Doi:10.1016/j.tetlet.2014.02.116
(2014)
Copper-catalyzed monoborylation of silylalkynes; Regio- and stereoselective synthesis of (Z)-β-(borylvinyl)silanes

Doi:10.1002/adsc.201300881
(2014)
Pyrrolo and pyrrolopyrimidine sulfonamides act as cytotoxic agents in hypoxia via inhibition of transmembrane carbonic anhydrases

Doi:10.1016/j.ejmech.2019.112021
(2020)
Soluble tetraarylporphyrin-platinum conjugates as cytotoxic and phototoxic antitumor agents

Doi:10.1021/jm0110690
(2002)
Synthesis of Heterometallic Species with (Ph2P)3CH or (Ph2P)3C(1-). Crystal Structures of >, > and >

Doi:10.1039/DT9940002891
(1994)

Article Doi