Supply the missing reagents and products in this three-reaction sequence in the middle of the synthesis. 1) I-B3 N. BrZnCH2CO2Et Grubbs-l P CH2CI2 (Ph3P)4Pd THF-DMPU, A 2) HOAC C11H16|NO C15H23NO3 C13H19NO3

Supply the missing reagents and products in this three-reaction sequence in the middle of the synthesis. 1) I-B3 N. BrZnCH2CO2Et Grubbs-l P CH2CI2 (Ph3P)4Pd THF-DMPU, A 2) HOAC C11H16|NO C15H23NO3 C13H19NO3

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.67P

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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

There are three steps in Somfai's short synthesis of the alkaloid, stemoamide.
Supply the missing reagents and products in this three-reaction sequence in the
middle of the synthesis.
H.
1) I-B:
BRZNCH2CO2ET
Grubbs-II
P
Q
R
CH2CI2
(Ph3P)4Pd
THF-DMPU, A
2) НОАС
C11H16|NO
C15H23NO3
C13H19NO3

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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.How many chiral centers are present in estrone?
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