Synthesis of (+/-)-Verrucarol Using a Remarkably Facile Alumina-Catalyzed Intramolecular Diels-Alder Reaction

DOI: 10.1021/jo00258a049

Source and publish data:

Journal of Organic Chemistry p. 5586 - 5588 (1988)

Update date:2022-07-31

Topics:

Authors:

Koreeda, Masato

Ricca, Daniel J.

Luengo, Juan I.

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

Article abstract of DOI:10.1021/jo00258a049

The synthesis of the verrucarol skeleton 3 has been achieved in a highly efficient and diastereoselective manner through the intramolecular Diels-Alder reaction of the cyclopentyl C-ring-tethered diene-dienophile 7.Remarkably, this intramolecular Diels-Alder reaction proceeds readily at room temperature under catalysis by neutral alumina.

Full text of DOI:10.1021/jo00258a049

Products guided by the article

Product name:2-((3S,3aR,5R,6aS)-3,3a-Dimethyl-4-methylene-2-oxo-3-phenylsulfanyl-hexahydro-cyclopenta[b]furan-5-yloxy)-3-hydroxy-4-methyl-pent-4-enoic acid ethyl ester

Cas No:117182-25-9

R&D Labs maybe for 117182-25-9

He Bei Shun Er Chemical Co., LTD.

Contact:86-0311-86996932/86860168

Address:No 18,North street
Wuxi Morality Chemical Co., Ltd(expird)

Contact:

Address:B/7F, 321th WuYun Rd, Wanda Plaza, Wuxi City, 214174, China
Quzhou Ruiyuan chemical Co., Ltd

Contact:+86-570-3039321/3039361/3039308

Address:18# Huayang Road,Quzhou High-tech Industrial Park, Zhejiang China.
CHANGYI CITY FENGRUN FINE CHEMICAL CO.,LTD

website:http://www.fengrunhuagong.com

Contact:+86-536-7869976

Address:Changyi Coastal Economic Development Zone
Jinan Hongfangde Pharmatech Co.LTD

Contact:0531-88870908

Address:F Bldg,750#,Shunhua Rd,New&High-tech Zone,Jinan,Shandong,China 250101

Relevant to this article

Heterocycles with a bridging nitrogen atom. 19. Development of routes for the synthesis of oxazoloisoquinolinium salts based on phenacylation of α-methyl-1(3)-isoquinolones

Doi:10.1007/s10593-009-0231-9
(2009)
An efficient synthesis of 3,3′-dipyridyl BINOL ligands

Doi:10.1016/j.tetlet.2009.04.092
(2009)
Synthesis and biological evaluation of 5-nitropyrimidine-2,4-dione analogues as inhibitors of nitric oxide and iNOS activity

Doi:10.1111/cbdd.12386
(2015)
Synthesis and base-pairing properties of C-nucleotides having 1-substituted 1H-1,2,3-triazoles

Doi:10.1016/j.bmcl.2009.04.063
(2009)
A versatile route to the tulearin class of macrolactones: synthesis of a stereoisomer of tulearin A

Doi:10.1021/ol900936t
(2009)
Microwave-induced by-products in the synthesis of 2-(4-methyl-2-phenylpiperazinyl)pyridine-3-carbonitrile

Doi:10.1016/j.tetlet.2009.05.068
(2009)

Article Doi