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Progesterone
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====Soy semisynthesis==== Progesterone can also be made from the [[stigmasterol]] found in [[soybean oil]] also. c.f. [[Percy Julian]]. [[File:Stigmasterol to progesterone synthesis.png|class=skin-invert-image|thumb| center |upright=3.65|[[Stigmasterol]] to progesterone synthesis.<ref name=Heyl>{{cite journal | vauthors = Heyl FW | title = Progesterone from 3-Acetoxybisnor-5-cholenaldehyde and 3-Ketobisnor-4-cholenaldehyde | journal = Journal of the American Chemical Society | volume = 72 | issue = 6 | pages = 2617β2619 | date = 1950 | doi = 10.1021/ja01162a076 | bibcode = 1950JAChS..72.2617H }}</ref><ref name="Slomp-1958">{{cite journal | vauthors = Slomp G | title = Ozonolysis. II. 1 The Effect of Pyridine on the Ozonolysis of 4,22-Stigmastadien-3-one 2 | journal = Journal of the American Chemical Society | volume = 80 | issue = 4 | pages = 915β921 | date = 1958 | doi = 10.1021/ja01537a041 | bibcode = 1958JAChS..80..915S }}</ref><ref name="pmid915584">{{cite journal | vauthors = Sundararaman P, Djerassi C | title = A convenient synthesis of progesterone from stigmasterol | journal = The Journal of Organic Chemistry | volume = 42 | issue = 22 | pages = 3633β3634 | date = October 1977 | pmid = 915584 | doi = 10.1021/jo00442a044 }}</ref><ref name="PBS.org-2007">{{cite web | url = https://www.pbs.org/wgbh/nova/transcripts/3402_julian.html | date = 6 February 2007 | title = Nova Transcripts: Forgotten Genius | publisher = PBS.org | access-date = 8 September 2017 | archive-date = 11 October 2018 | archive-url = https://web.archive.org/web/20181011224654/http://www.pbs.org/wgbh/nova/transcripts/3402_julian.html | url-status = live }}</ref><ref name="lipidlibrary.aocs.org">{{cite web | url = http://lipidlibrary.aocs.org/history/Julian/index.htm | title = Giants of the Past | publisher = lipidlibrary.aocs.org | url-status = dead | archive-url = https://web.archive.org/web/20120415001340/http://lipidlibrary.aocs.org/history/Julian/index.htm | archive-date = 15 April 2012 }}</ref>]]
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