Alkylated Steroids. Part 4. An Unusual Favorskii Rearrangement

DOI: 10.1039/P19810002631

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2631 - 2636 (1981)

Update date:2022-08-03

Topics:

Authors:

Logan, Robert T.

Roy, Robert G.

Woods, Gilbert F.

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

Article abstract of DOI:10.1039/P19810002631

Favorskii rearrangement of the mixed 17ξ-bromo-16α-methyl-20-oxo-5α-pregn-9(11)-en-3β-yl acetates (5) and (6) (9:1) gives methyl 3β-hydroxy-16α,17α-dimethyl-5α-androst-9(11)-ene-17-carboxylate (7) and methyl 3β-hydroxy-16α-methyl-5α-pregn-9(11)-en-21-oate (9) as the major components.Only a small amount of the isomeric 16α,17β-dimethyl-17-carboxylate (8) is formed.The structures of the esters (7) and (9) are confirmed by synthesis, and an explanation for the unexpected formation of (9) is advanced.

Full text of DOI:10.1039/P19810002631

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:Toluene-4-sulfonic acid 2-[(3S,5S,8S,10S,13R,14S,16R,17S)-10,13,16-trimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethyl ester

Cas No:80055-36-3

R&D Labs maybe for 80055-36-3

Anqing World Chemical Co., Ltd.

Contact:+86-556-5800026

Address:Daguan Economic Development Zone of circular economy industrial park Anqing City Anhui province
Hunan Dinuo Pharmaceutical Co.,Ltd.

Contact:86-731-88280100*8561

Address:Bio-pharmaceutical industrial park, Liuyang, Hunan, China
GrainPlusKft

Contact:36-307-428048

Address:Kulterulet hrsz 09/44, Tatahaza
Daqing New Century Fine Chemical Co., Ltd.(expird)

Contact:010-57126694

Address:No.39, jinxing cun, honggang district
shanghai jinshan pharmaceutical Co.,Ltd

Contact:021-57363011，13681638167

Address:No. 7966 Tingfeng Road,Jinshan,Shanghai,China

Relevant to this article

Thermochemistry for the Gas-Phase Ion-Molecule Clustering of CO2⁺CO2, SO2⁺CO2, N2O⁺N2O, O2⁺CO2, NO⁺CO2, O2⁺N2O, and NO⁺N2O: Description of a New Hybrid Drift Tube/Ion Scoure with Coaxial Electron Beam and Ion Exit Apertures

Doi:10.1021/j100321a037
(1988)
Adriamycin analogues. Preparation and biological evaluation of some N-perfluoroacyl analogues of daunorubicin, adriamycin, and N-(trifluoroacetyl)adriamycin 14-valerate and their 9,10-anhydro derivatives

Doi:10.1021/jm00344a019
(1982)
Gibbilimbol analogues as antiparasitic agents - Synthesis and biological activity against Trypanosoma cruzi and Leishmania (L.) infantum

Doi:10.1016/j.bmcl.2016.01.040
(2016)
STRUCTURE ELUCIDATION AND SYNTHESIS OF (2S)-4-OXO-1-AZABICYCLO<3.3.0>OCTA-5,7-DIENE-2-CARBOXYLIC ACID, A NEW METABOLITE ISOLATED FROM STREPTOMYCES OLIVACEUS

Doi:10.1016/S0040-4039(01)81888-8
(1981)
AN UNUSUAL REACTION OF TRIPHENYLMETHYLSULFENYL CHLORIDE WITH NORBORNENE AND NORBORNADIENE

Doi:10.1016/S0040-4039(01)81986-9
(1981)
Synthesis of 4-[(2-imidazylethynyl)]-5-(2-pyridylethynyl)veratrole and characterization of the coordination complexes with silver(I) and palladium(II)

Doi:10.1016/j.ica.2019.119328
(2020)

Article Doi