Identify compounds A and B, two synthetic intermediates in the 1979 synthesis of the plant growth hormone gibberellic acid by Corey and Smith. Gibberellic acid induces cell division and elongation, thus making plants tall and leaves large. [1] Og NaOH several steps B [2] (CH3)2S E:OH C15H2204 OH HO ČOH gibberellic acid

Identify compounds A and B, two synthetic intermediates in the 1979 synthesis of the plant growth hormone gibberellic acid by Corey and Smith. Gibberellic acid induces cell division and elongation, thus making plants tall and leaves large. [1] Og NaOH several steps B [2] (CH3)2S E:OH C15H2204 OH HO ČOH gibberellic acid

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

Chapter23: Amines

Section: Chapter Questions

Problem 23.60P: Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for...

See similar textbooks

Similar questions

The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?
(S)-Glutamic acid is one of the 20 amino acid building blocks of polypeptides and proteins (Chapter 27). Propose a mechanism for the following conversion.
Suppose we aempt the conversion of fumaric acid to deuterated malic acid with BD3·THF,followed by oxidation with D2O2in NaOD(aq). Show all the possible stereoisomers (as Fisherprojections) that may be formed, and draw the mechanistic pathways (showing stereochemistry)that lead to these possible products
Treatment of cholesterol with mCPBA results in formation of a single epoxide A, with the stereochemistry drawn. Why isn’t the isomeric epoxide B formed to any extent?
The last step in the synthesis of β-vetivone, a major constituent of vetiver, a perennial grass found in tropical and subtropical regions of the world, involves treatment of C with CH3Li to form an intermediate X, which forms β-vetivone with aqueous acid. Identify the structure of X and draw a mechanism for converting X to β-vetivone.
Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B alsoreacts with warm nitric acid to give an optically active aldaric acid, but A reacts to givean optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, whichgives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D isdegraded to (+)@glyceraldehyde. Deduce the structures of sugars A, B, C, and D, and useFigure 23-3 to determine the correct names of these sugars.
trehalose is a disacharide that can be obtained from fungi sea uchins and insects. acid hydrolysis of trehalose yields only D-glucose. trehalose is hydrolysed by a-glucosidase but not b-glucosidase.methylation of trhalose followed by hydrolysis yield two molar equivalents of 2-3-4-6 -tetra-O-methyl-D-glucopyranose. deduce the structure of the trehalose using the experimental data
An optically active D-aldopentose (A) produced an optically inactive alditol (B) upon treatment with H2/Pt. When the aldopentose (A) was subjected to a Ruff degradation, D-aldotetrose (C) was generated. The aldotetrose (C) gave an optically active aldaric acid (D) upon oxidation with HNO3. D-aldopentose (A) can be prepared from D-threose by a Killani Fischer synthesis. Propose structure of A through D.
Explain this result: Acetic acid (CH3COOH), labeled at its OH oxygen with the uncommon 18O isotope (shown in red), was treated with aqueousbase, and then the solution was acidified. Two products having the 18Olabel at different locations were formed.
Choose the product that is expected when the β-pyranose form of compound A is treated with excess ethyl iodide in the presence of silver oxide. The following information can be used to determine the identity of compound A: 1. The molecular formula of compound A is C6H12O6.2. Compound A is a reducing sugar.3. When compound A is subjected to a Wohl degradation two times sequentially, D-erythrose is obtained.4. Compound A is epimeric with D-glucose at C3.5. The configuration at C2 is R.
When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose