Preparation of 9.9-dimethoxytetracyclo[8.5.0.0]pentadeca- 3,5,12,14,-tetraene and conversion to hexacyclo[8.5.1.1.0.0.0.0]heptadeca -2,8-diene-13-one using a domino Diels-Alder reaction

Thomas D. Golobish, Jennifer K. Burke, Alfred H. Kim, Sung W. Chong, E. Loren Probst, Patrick J. Carroll, William P. Dailey

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The easily prepared bishomosecoheptaprismane ring system of 1 was converted to the tetracyclo[8.5.0.02,8.97,11]pentadeca-3,5,12,14- tetraene ring system of 10 using a photochemical decarbonylation/fragmentation reaction as the key step. The closely held face-to-face butadiene units in 10 undergo [4+4]cycloaddition under photochemical conditions and participate in domino Diels-Alder reactions with maleic anhydride and dicyanoacetylene. The maleic anhydride domino Diels- Alder adduct 18 was converted to the previously unreported hexacyclo[8.5.1.14,7.05,14.06,16.011,15.016 ,17]heptadeca ne ring system embodied in 19. A single crystal X-my analysis of 20, one member of this new ring system, is reported and the results are compared with ab initio molecular orbital calculations.

Original languageEnglish
Pages (from-to)7013-7024
Number of pages12
JournalTetrahedron
Volume54
Issue number25
DOIs
StatePublished - Jun 18 1998
Externally publishedYes

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