Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A three-step route to a tricyclic steroid precursor.

Literature DB >> 18816101

A three-step route to a tricyclic steroid precursor.

Abstract

2-Alkyl cyclohexenones are useful intermediates for organic synthesis. The Wittig reaction of a series of aldehydes with (cyclopropylmethyl)triphenylphosphonium bromide delivered the corresponding alkenyl cyclopropanes. UV irradiation in the presence of Fe(CO)5 converted the alkenyl cyclopropanes to the 2-substituted cyclohexenones. This approach enabled a three-step synthesis of the tricyclic core of estrone methyl ether.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18816101 PMCID： PMC2654412 DOI： 10.1021/jo801767n

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

9 in total

1. Formal enantioselective synthesis of (+)-estrone.

Authors: Darunee Soorukram; Paul Knochel
Journal: Org Lett Date: 2007-02-13 Impact factor: 6.005

2. [Not Available].

Authors: G ANNER; K MIESCHER
Journal: Helv Chim Acta Date: 1948-12-01 Impact factor: 2.164

3. Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C.

Authors: François-Xavier Felpin
Journal: J Org Chem Date: 2005-10-14 Impact factor: 4.354

4. Synthesis of (-)-delobanone.

Authors: D F Taber; G Bui; B Chen
Journal: J Org Chem Date: 2001-05-18 Impact factor: 4.354

5. Determinants of retinoid X receptor transcriptional antagonism.

Authors: Claudio N Cavasotto; Gang Liu; Sharon Y James; Peter D Hobbs; Valerie J Peterson; Ananyo A Bhattacharya; Siva K Kolluri; Xiao-kun Zhang; Mark Leid; Ruben Abagyan; Robert C Liddington; Marcia I Dawson
Journal: J Med Chem Date: 2004-08-26 Impact factor: 7.446

6. Rhodium-catalyzed intramolecular hydroacylation of 5- and 6-alkynals: convenient synthesis of alpha-alkylidenecycloalkanones and cycloalkenones.

Authors: Kenzo Takeishi; Koudai Sugishima; Kaori Sasaki; Ken Tanaka
Journal: Chemistry Date: 2004-11-05 Impact factor: 5.236

7. Simple, catalytic enantioselective syntheses of estrone and desogestrel.

Authors: Qi-Ying Hu; Pankaj D Rege; E J Corey
Journal: J Am Chem Soc Date: 2004-05-19 Impact factor: 15.419

8. A total synthesis of estrone based on a novel cascade of radical cyclizations.

Authors: Gerald Pattenden; Miguel A Gonzalez; Stuart McCulloch; Affo Walter; Steven J Woodhead
Journal: Proc Natl Acad Sci U S A Date: 2004-08-10 Impact factor: 11.205

9. 2,5-Dialkyl cyclohexenones by Fe(CO)5-mediated carbonylation of alkenyl cyclopropanes: functional group compatibility.

Authors: Douglass F Taber; Pramod V Joshi; Kazuo Kanai
Journal: J Org Chem Date: 2004-04-02 Impact factor: 4.354

9 in total

7 in total

1. Enantioselective conjugate allylation of cyclic enones.

Authors: Douglass F Taber; David A Gerstenhaber; James F Berry
Journal: J Org Chem Date: 2011-08-23 Impact factor: 4.354

2. Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis.

Authors: William A Donaldson; Subhabrata Chaudhury
Journal: European J Org Chem Date: 2009-08

3. The enantioselective construction of tetracyclic diterpene skeletons with Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation reactions.

Authors: Sarah J Burke; William P Malachowski; Sharan K Mehta; Roselyn Appenteng
Journal: Org Biomol Chem Date: 2015-03-07 Impact factor: 3.876