Tandem Cope-Claisen Rearrangement in the Synthesis of Steroids: Storck's Keto Acid

DOI: 10.1021/jo00192a006

Source and publish data:

Journal of Organic Chemistry p. 3278 - 3281 (1984)

Update date:2022-07-31

Topics:

Authors:

Ziegler, Frederick E.

Lim, Hong

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

Article abstract of DOI:10.1021/jo00192a006

The tandem Cope-Claisen rearrangement of triene 3 affords aldehydes 4a and 5a (4/1 ratio) upon thermolysis at 300 deg C.Aldehyde 4a is subjected to intramolecular alkylation leading to Storck's keto acid 15, an important intermediate in the synthesis of corticosteroids.

Full text of DOI:10.1021/jo00192a006

Products guided by the article

Product name:Toluene-4-sulfonic acid (S)-2-{(1S,2S)-2-[2-cyano-2-(1-ethoxy-ethoxy)-ethyl]-2-methyl-3-methylene-cyclopentyl}-but-3-enyl ester

Cas No:91202-57-2

R&D Labs maybe for 91202-57-2

Chengdu Boon Stream Chemical Industry Co.,Ltd.

Contact:+86-28-83156758

Address:No.859,Dongzikou Road,Jinniu District,Chengdu,Sichuan,P.R.China
Jiangxi Dongbang Pharmaceutical Co., Ltd.

Contact:+86-795-4433603, 4433388

Address:Fengxin Industrial Park, Fengxin County, Jiangxi Province, P.R.C
ENERGYCO LTD.

Contact:+86-25-83719363

Address:106-7 Chunnan Rd, Chunxi Town, Gaochun, Nanjing, China
Shanghai UCHEM Inc.

Contact:+86-21-56338808

Address:799 Dunhuang Road, Putuo
QINGDAO TAOSIGN INTERNATIONAL TRADE CO.,LIMITED

Contact:+86-0532-82683616

Address:RM1402, Doublestar Seacoase 7#, No. 5 Guizhou Road, Qingdao, Shandong, China

Relevant to this article

Synthesis and Structure of a Stable Complex Featuring an S-Bound Dibenzothiophene Ligand: RuCl2(4-R2P(DBT))2 (DBT = Dibenzothiophene)

Doi:10.1021/ja00330a073
(1984)
Nucleosides with self-complementary hydrogen-bonding motifs: Synthesis and base-pairing studies of two nucleosides containing the imidazo[4,5-d]pyridazine ring system

Doi:10.1016/j.bmc.2006.05.043
(2006)
Quinolinone and pyridopyrimidinone inhibitors of DNA-dependent protein kinase

Doi:10.1039/b705095j
(2007)
Oxidation of aromatic compounds: XIV. Oxidation of arylethynyl ketones in the system CF₃CO₂H-CH₂Cl₂-PbO ₂

Doi:10.1134/S1070428006010118
(2006)
Synthesized pyridine compound derivatives decreased TNF alpha and adhesion molecules and ameliorated HSV-induced inflammation in a mouse model

Doi:10.1016/j.ejphar.2011.01.062
(2011)
Mo (CO)₆-assisted Pd-supported magnetic graphene oxide-catalyzed carbonylation-cyclization as an efficient way for the synthesis of 4(3H)-quinazolinones

Doi:10.1002/aoc.4769
(2019)

Article Doi