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Silvocarcin M is isolated from Streptomyces strains and has strong antitumor activity. OMe OH OMe H OH OH CH3 H3C OH Gilvocarcin M Suzuki and coworkers were able to carry out the total synthesis of naturally occurring (-)-gilvocarcin M. Their synthesis included the following steps. (The wavy line means that stereochemistry is unspecified or is a mixture.) The stereochemistry of the product appears to be counterintuitive (apparent attack from the more hindered side). The rea- son is that the reaction involves initial O-alkylation followed by a rearrangement that need not concern us. OBn OBn H OBn H OBn OBn CH Lewis acid HO OBn CH AcO we НО Bn = CH,Ph OBn OBn %3! (A) (В) The next step involves triflation and treatment with butyl lithium. OBn H OBn TI,O Buli. -Pr, NEt -78"C Но OBn "CH (D) (B) OBn Tf = CF SO,

Silvocarcin M is isolated from Streptomyces strains and has strong antitumor activity. OMe OH OMe H OH OH CH3 H3C OH Gilvocarcin M Suzuki and coworkers were able to carry out the total synthesis of naturally occurring (-)-gilvocarcin M. Their synthesis included the following steps. (The wavy line means that stereochemistry is unspecified or is a mixture.) The stereochemistry of the product appears to be counterintuitive (apparent attack from the more hindered side). The rea- son is that the reaction involves initial O-alkylation followed by a rearrangement that need not concern us. OBn OBn H OBn H OBn OBn CH Lewis acid HO OBn CH AcO we НО Bn = CH,Ph OBn OBn %3! (A) (В) The next step involves triflation and treatment with butyl lithium. OBn H OBn TI,O Buli. -Pr, NEt -78"C Но OBn "CH (D) (B) OBn Tf = CF SO,

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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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Give a structure for (C).

Silvocarcin M is isolated from Streptomyces strains and has strong antitumor activity. OMe OH OMe H OH OH CH3 H3C OH Gilvocarcin M Suzuki and coworkers were able to carry out the total synthesis of naturally occurring (-)-gilvocarcin M. Their synthesis included the following steps. (The wavy line means that stereochemistry is unspecified or is a mixture.) The stereochemistry of the product appears to be counterintuitive (apparent attack from the more hindered side). The rea- son is that the reaction involves initial O-alkylation followed by a rearrangement that need not concern us. OBn OBn H OBn H OBn OBn CH Lewis acid HO OBn CH AcO we НО Bn = CH,Ph OBn OBn %3! (A) (В)
Transcribed Image Text:Silvocarcin M is isolated from Streptomyces strains and has strong antitumor activity. OMe OH OMe H OH OH CH3 H3C OH Gilvocarcin M Suzuki and coworkers were able to carry out the total synthesis of naturally occurring (-)-gilvocarcin M. Their synthesis included the following steps. (The wavy line means that stereochemistry is unspecified or is a mixture.) The stereochemistry of the product appears to be counterintuitive (apparent attack from the more hindered side). The rea- son is that the reaction involves initial O-alkylation followed by a rearrangement that need not concern us. OBn OBn H OBn H OBn OBn CH Lewis acid HO OBn CH AcO we НО Bn = CH,Ph OBn OBn %3! (A) (В)
The next step involves triflation and treatment with butyl lithium. OBn H OBn TI,O Buli. -Pr, NEt -78"C Но OBn "CH (D) (B) OBn Tf = CF SO,
Transcribed Image Text:The next step involves triflation and treatment with butyl lithium. OBn H OBn TI,O Buli. -Pr, NEt -78"C Но OBn "CH (D) (B) OBn Tf = CF SO,
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Tf2O is trifluoromethanesulfonic anhydride.

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