Equilenin

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Equilenin
Equilenin.svg
Clinical data
Synonyms 6,8-Didehydroestrone; Estra-1,3,5(10),6,8-pentaen-3-ol-17-one
Routes of
administration
By mouth
Drug class Estrogen
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
KEGG
ChEMBL
ECHA InfoCard 100.007.483 Edit this at Wikidata
Chemical and physical data
Formula C18H18O2
Molar mass 266.339 g/mol
3D model (JSmol)
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Equilenin, also known as 6,8-didehydroestrone, as well as estra-1,3,5(10),6,8-pentaen-3-ol-17-one, is a naturally occurring steroidal estrogen obtained from the urine of pregnant mares.[1][2] It is used as one of the components in conjugated estrogens (brand name Premarin),[2] it was the first complex natural product to be fully synthesized, in work reported by 1940 by Bachmann and Wilds.[3]

Chemistry[edit]

Synthesis[edit]

Total synthesis[edit]

The synthesis developed by the Bachmann group started from Butenand's ketone[4] – the 7-methoxy structural analog of 1,2,3,4-tetrahydrophenanthren-1-one[5] – and which can be readily prepared from 1,6-Cleve's acid.[6] The approach was based on well-established transformations like the Claisen condensation, the Reformatsky reaction, the Arndt–Eistert reaction, and the Dieckmann condensation.[3] Nicolaou described this preparation as ending the era preceding the post-World War II work of Robert Burns Woodward that introduced enantioselective synthesis;[4] in this synthesis, a mixture of stereoisomers were prepared and then resolved,[6] and the choice of target was partly because of the existence of only two chiral carbons and hence only four stereoisomers.[5]

Bachmann's total synthesis of equilenin.jpg

The overall yield of the synthesis was 2.7% based on a twenty-step process starting from Cleve's acid.[6]

See also[edit]

References[edit]

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 494–. ISBN 978-1-4757-2085-3. 
  2. ^ a b Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 751–. ISBN 978-1-4511-4847-3. 
  3. ^ a b Bachmann, Werner E.; Cole, Wayne; Wilds, Alfred L. (1940). "The Total Synthesis of the Sex Hormone Equilenin and Its Stereoisomers". J. Am. Chem. Soc. 62 (4): 824–839. doi:10.1021/ja01861a036. 
  4. ^ a b Nicolaou, Kyriacos C.; Vourloumis, Dionisios; Winssinger, Nicolas; Baran, Phil S. (2000). "The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century" (PDF). Angew. Chem. Int. Ed. 39 (1): 44–122. doi:10.1002/(SICI)1521-3773(20000103)39:1<44::AID-ANIE44>3.0.CO;2-L. 
  5. ^ a b Bachmann, Werner E.; Cole, Wayne; Wilds, Alfred L. (1939). "The Total Synthesis of the Sex Hormone Equilenin". J. Am. Chem. Soc. 61 (4): 974–975. doi:10.1021/ja01873a513. 
  6. ^ a b c Nakanishi, Koji (1974). "Steroids". In Nakanishi, Koji; Goto, Toshio; Itô, Shô; Natori, Shinsaku; Nozoe, Shigeo. Natural Products Chemistry. 1. Academic Press. pp. 421–545.