CI H3CO H3CO OCH, 1. NaH, THF CN КОН/Н,О 2. MEOCH,CI, THF DMSO (A) (В) (C) ČN (D) COOH H3CO ARCO,H 1. КОН/Н,О L/KI, NaHCO, NaHCO,,CH,CI, 2. CO, OMe H,O OMe НО (F) НО (G) (E) Ac,O Pyridine BugSnH BBr, CrO, Pyridine OMe OMe ОН СНО AcO (H) AcO (I) AcO (J) AcO (К) (Corey lactone)

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined.

Q. What is the function of the carbon dioxide added to the reaction mixture in Step 2 of the conversion of (E) to (F)? Hint: What happens when carbon dioxide is dissolved in water? Why not just use HCl?

CI
H3CO
H3CO
OCH,
1. NaH, THF
CN
КОН/Н,О
2. MEOCH,CI, THF
DMSO
(A)
(В)
(C)
ČN
(D)
COOH
H3CO
ARCO,H
1. КОН/Н,О
L/KI, NaHCO,
NaHCO,,CH,CI,
2. CO,
OMe
H,O
OMe
НО
(F)
НО
(G)
(E)
Ac,O
Pyridine
BugSnH
BBr,
CrO,
Pyridine
OMe
OMe
ОН
СНО
AcO
(H)
AcO
(I)
AcO
(J)
AcO
(К)
(Corey lactone)
Transcribed Image Text:CI H3CO H3CO OCH, 1. NaH, THF CN КОН/Н,О 2. MEOCH,CI, THF DMSO (A) (В) (C) ČN (D) COOH H3CO ARCO,H 1. КОН/Н,О L/KI, NaHCO, NaHCO,,CH,CI, 2. CO, OMe H,O OMe НО (F) НО (G) (E) Ac,O Pyridine BugSnH BBr, CrO, Pyridine OMe OMe ОН СНО AcO (H) AcO (I) AcO (J) AcO (К) (Corey lactone)
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