Intramolecular Nicholas Reactions in the Synthesis of Dibenzocycloheptanes. Synthesis of Allocolchicine NSC 51046 and Analogues and the Formal Synthesis of (−)-Allocolchicine

Authors

Sinisa Djurdjevic, University of WindsorFollow
Fei Yang, University of Windsor
James R. Green, University of WindsorFollow

Document Type

Article

Publication Date

12-3-2010

Publication Title

Journal of Organic Chemistry

Volume

75

Issue

23

First Page

8241

Last Page

8251

Abstract

The preparation of dibenzocycloheptyne-Co₂(CO)₆ complexes by intramolecular Nicholas reactions of biaryl-2-propargyl alcohol-Co₂(CO)₆ derivatives is described. Reductive decomplexation of the dibenzocycloheptyne-Co₂(CO)₆ complexes affords the corresponding dibenzocycloheptenes, individual members of which have been employed in a formal total synthesis of (−)-allocolchicine, the preparation of 6,7-dihydro-3,4,9,10,11-pentamethoxy-5H-dibenzo[a,c]cyclohepten-5-one, and the enantioselective total syntheses of NSC 51046 and its 3,8,9,10-tetramethoxy regioisomer.

DOI

10.1021/jo101953n

Funding Reference Number

NSERC

Comments

This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see DOI: 10.1021/jo101953n at http://pubs.acs.org/doi/abs/10.1021/jo101953n.

Recommended Citation

Djurdjevic, Sinisa; Yang, Fei; and Green, James R.. (2010). Intramolecular Nicholas Reactions in the Synthesis of Dibenzocycloheptanes. Synthesis of Allocolchicine NSC 51046 and Analogues and the Formal Synthesis of (−)-Allocolchicine. Journal of Organic Chemistry, 75 (23), 8241-8251.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/76