A very short synthesis of 3-methoxyestra-1,3,5,8,14-pentaen-17-one

D. Jean Burnell; Yong-Jin Wu

doi:10.1139/v89-125

A very short synthesis of 3-methoxyestra-1,3,5,8,14-pentaen-17-one

Canadian Journal of Chemistry ◽

10.1139/v89-125 ◽

1989 ◽

Vol 67 (5) ◽

pp. 816-819 ◽

Cited By ~ 7

Author(s):

D. Jean Burnell ◽

Yong-Jin Wu

Keyword(s):

Lewis Acid ◽

Catalysed Reaction ◽

Short Synthesis

3-Methoxyestra-1,3,5,8,14-pentaen-17-one (4) was prepared from 6-methoxy-1-tetralone (8) by an efficient two-pot procedure in which the D ring was generated by the Lewis acid catalysed reaction of 1,2-bis(trimethylsiloxy)cyclobutene (5) with an appropriate ketal (10). Keywords: steroid, estrone, annellation.

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Synthesis of squaric acid derivatives by Lewis acid-catalysed reaction of its dichloride, methyl ester chloride, diethylamide chloride, and ethyl diester with unsaturated organosilanes: new method for C–C bond formation on cyclobutenedione

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19930000263 ◽

1993 ◽

pp. 263-271 ◽

Cited By ~ 19

Author(s):

Masatomi Ohno ◽

Yoshihiko Yamamoto ◽

Yuhichi Shirasaki ◽

Shoji Eguchi

Keyword(s):

Methyl Ester ◽

Lewis Acid ◽

Bond Formation ◽

New Method ◽

Squaric Acid ◽

Catalysed Reaction

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ChemInform Abstract: Lewis Acid-Promoted Ring-Opening Allylation of Epichlorohydrin (I) with Allylic Silanes (II) and Stannanes (VI) to Afford 1-Chloro-5- alken-2-ols (III). A Short Synthesis of (S)-(-)-Ipsenol.

ChemInform ◽

10.1002/chin.199104155 ◽

2010 ◽

Vol 22 (4) ◽

pp. no-no

Author(s):

T. IMAI ◽

S. NISHIDA

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Allylic Silanes ◽

Short Synthesis

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Lewis acid-catalysed reaction of (cyclo)alkenes with oxiranes

Tetrahedron Letters ◽

10.1016/s0040-4039(99)02253-4 ◽

2000 ◽

Vol 41 (9) ◽

pp. 1483-1486 ◽

Cited By ~ 6

Author(s):

David Munro ◽

Chris Newman

Keyword(s):

Lewis Acid ◽

Catalysed Reaction

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Lewis acid-catalyzed, high pressure, stereospecific, regiospecific, Diels-Alder cycloaddition of unsubstituted 2-pyrone: Short synthesis of a racemic A-ring precursor to physiologically active 1-hydroxyvitamin D3 steroids

Tetrahedron Letters ◽

10.1016/s0040-4039(00)78339-0 ◽

1994 ◽

Vol 35 (41) ◽

pp. 7545-7548 ◽

Cited By ~ 19

Author(s):

Gary H. Posner ◽

Yuji Ishihara

Keyword(s):

High Pressure ◽

Lewis Acid ◽

Diels Alder ◽

Short Synthesis ◽

Acid Catalyzed

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Lewis-Acid-Catalysed Reaction of 3-Hydroxy-2-oxindoles with Terminal Alkynes: Synthetic Approaches to the Pyrroloindoline Alkaloids

European Journal of Organic Chemistry ◽

10.1002/ejoc.201700507 ◽

2017 ◽

Vol 2017 (21) ◽

pp. 3078-3091 ◽

Cited By ~ 7

Author(s):

Lakshmana K. Kinthada ◽

K. Naresh Babu ◽

Dikshaa Padhi ◽

Alakesh Bisai

Keyword(s):

Lewis Acid ◽

Terminal Alkynes ◽

Catalysed Reaction ◽

Synthetic Approaches

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Lewis acid promoted ring-opening allylation of epichlorohydrin with allylic silanes and stannanes to afford 1-chloro-5-alken-2-ols. A short synthesis of (S)-(-)-ipsenol

The Journal of Organic Chemistry ◽

10.1021/jo00303a018 ◽

1990 ◽

Vol 55 (16) ◽

pp. 4849-4852 ◽

Cited By ~ 43

Author(s):

Toshiro Imai ◽

Shinya Nishida

Keyword(s):

Lewis Acid ◽

Ring Opening ◽

Allylic Silanes ◽

Short Synthesis

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ChemInform Abstract: On the Lewis Acid-Catalysed Reaction of the 2,3-Bis(trimethylstannyl)- 1-alkene Moiety with Aldehydes.

ChemInform ◽

10.1002/chin.199138239 ◽

2010 ◽

Vol 22 (38) ◽

pp. no-no

Author(s):

T. N. MITCHELL ◽

U. SCHNEIDER ◽

K. HEESCHE-WAGNER

Keyword(s):

Lewis Acid ◽

Catalysed Reaction

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Lewis acid catalysed reaction of aliphatic thiols with thiophosgene

Journal of the Chemical Society Perkin Transactions 1 ◽

10.1039/p19740001308 ◽

1974 ◽

pp. 1308 ◽

Cited By ~ 8

Author(s):

Nils H. Nilsson

Keyword(s):

Lewis Acid ◽

Catalysed Reaction ◽

Aliphatic Thiols

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On the Lewis acid-catalysed reaction of the 2,3-bis(trimethylstannyl)-1-alkene moiety with aldehydes

Journal of Organometallic Chemistry ◽

10.1016/0022-328x(91)86010-n ◽

1991 ◽

Vol 411 (1-2) ◽

pp. 107-120 ◽

Cited By ~ 9

Author(s):

Terence N. Mitchell ◽

Ulrich Schneider ◽

Kerstin Heesche-Wagner

Keyword(s):

Lewis Acid ◽

Catalysed Reaction

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Formation of 2,2-disubstituted 1,3-cyclopentanediones from ketals with 1,2-bis(trimethylsilyloxy)cyclobutene

Canadian Journal of Chemistry ◽

10.1139/v93-169 ◽

1993 ◽

Vol 71 (9) ◽

pp. 1311-1318 ◽

Cited By ~ 13

Author(s):

Yong-Jin Wu ◽

Dean W. Strickland ◽

Tracy J. Jenkins ◽

Pei-Ying Liu ◽

D. Jean Burnell

Keyword(s):

Double Bond ◽

Carbonyl Group ◽

Lewis Acid ◽

Steric Hindrance ◽

Catalysed Reaction ◽

Carbon Double Bond ◽

Direct Formation

The direct formation of 2,2-disubstituted 1,3-cyclopentanedione compounds by a Lewis acid catalysed reaction with 1,2-bis(trimethylsilyloxy)cyclobutene proceeds in good to excellent yields with unhindered ketals, but steric hindrance reduces the yields considerably. A carbonyl group α or β to the ketal, or a carbon–carbon double bond α to the ketal, stops the reaction completely. Orthoesters do not give geminally acylated products in synthetically useful yields.

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