O!Bu two Heck reactions (2) + (3) H HO MeO Estrone (1)

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
Section14.SE: Something Extra
Problem 65AP: The double bond of an enamine (alkene + amine) is much more nucleophilic than a typical alkene...
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Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone.

Q.Show how your proposals for compounds (2) and (3) can be converted to compound (1). (Note: In the course of developing this synthesis, Tietze discovered that vinylic bromides and iodides are more reactive in Heck reactions than are aryl bromides and iodides.)

O!Bu
two Heck
reactions
(2)
+ (3)
H
HO
MeO
Estrone
(1)
Transcribed Image Text:O!Bu two Heck reactions (2) + (3) H HO MeO Estrone (1)
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