Remote asymmetric induction in an intramolecular ionic Diels-Alder reaction: application to the total synthesis of (+)-dihydrocompactin. Journal Article uri icon



  • The total synthesis of (+)-dihydrocompactin via an intramolecular ionic Diels-Alder reaction that proceeds with remote stereocontrol is described. This reaction proceeds by an intermediate vinyl-oxocarbenium ion (6), the conformational constraints of which lead to the observed asymmetric induction. The sense of asymmetric induction appears contrasteric and is explained by the proposed reactive conformation shown in Figure 1.

publication date

  • May 1, 2005

has restriction

  • closed

Date in CU Experts

  • September 6, 2013 5:00 AM

Full Author List

  • Sammakia T; Johns DM; Kim G; Berliner MA

author count

  • 4

citation count

  • 3

Other Profiles

International Standard Serial Number (ISSN)

  • 0002-7863

Electronic International Standard Serial Number (EISSN)

  • 1520-5126

Additional Document Info

start page

  • 6504

end page

  • 6505


  • 127


  • 18