11. A radical cyclization cascade was used in the total synthesis of the natural product, hirsutene. Propose a mechanism for this transformation. Hints: a) Start by using the tin radical (left) to abstract the iodide. b) After both new rings are formed, an H atom can be abstracted from Bu3Sn-H to complete the mechanism. Bu,SnH AİBN BuzSn' benzene 80 °C H 80% yield hirsutene

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
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.63P
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11. A radical cyclization cascade was used in the total synthesis of the natural product, hirsutene. Propose a
mechanism for this transformation. Hints: a) Start by using the tin radical (left) to abstract the iodide. b) After
both new rings are formed, an H atom can be abstracted from Bu3Sn-H to complete the mechanism.
BuzSnH
AIBN
Bu,Sn
benzene
80 °C
80% yield
hirsutene
Transcribed Image Text:11. A radical cyclization cascade was used in the total synthesis of the natural product, hirsutene. Propose a mechanism for this transformation. Hints: a) Start by using the tin radical (left) to abstract the iodide. b) After both new rings are formed, an H atom can be abstracted from Bu3Sn-H to complete the mechanism. BuzSnH AIBN Bu,Sn benzene 80 °C 80% yield hirsutene
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