{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Syn or an7 in tricyclic product i h h h h 1 hirustene

Info icon This preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: bonds formed –  2 conFguous stereogenic centers formed –  2 carbocyclic rings formed Nicolaou, Classics in Total Synthesis, 1996 9 Retrosynthetic Analysis and Strategy of hirsutene •  133132131 (5 ­exo ­radical cyclizaFon) –  Must proceed in a cis fashion H  TransiFon state to strained H 5-exo-dig H 131 5-exo-dig radical cyclization radical cyclization H H 132 H H 133 H trans ­fused bicyclo[3.3.0]octane does not permit overlap between SOMO and LUMO of the alkene. •  Side chains in monocyclic radical, 134 dictates 2 outer ring relaFonships. –  syn or an7 in tricyclic product I H H H H 1: hirustene H –  cis ­an7 ­cis ring fusion stereochemistry arises naturally from cyclizaFon precurser with trans ­disposed side chains. 10 134 Nicolaou, Classics in Total Synthesis, 1996 Retrosynthetic Analysis and Strategy of hirsutene •  trans ­DisubsFtuted cyclopentene, 134 retrosyntheFcally from –  Organmetallic reagent –  cis ­fused bicyclic la...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern