Document Type

Article

Publication Date

12-3-2010

Publication Title

Journal of Organic Chemistry

Volume

75

Issue

23

First Page

8258

Last Page

8270

DOI

10.1021/jo102127q

Abstract

The application of the Nicholas reaction chemistry of 2,7-dioxygenated naphthalenes in the synthesis of cyclohepta[de]napthalenes and in the synthesis of (±)-microstegiol (1) is presented. The substitution profile of Nicholas monosubstitution (predominantly C-1) and disubstitution reactions (predominantly 1,6-) on 2,7-dioxygenated napthalenes is reported. Application of a 1,8-dicondensation product and selected C-1 monocondensation products to the construction of cyclohepta[de]naphthalenes by way of ring closing metathesis and intramolecular Friedel−Crafts reactions, respectively, is described. Deprotection of the C-7 oxygen function to the corresponding naphthol allows tautomerization to cyclohepta[de]naphthalene-1-ones upon seven-membered-ring closure in most cases, and replacement of the C-2 oxygen function in the naphthalene by a methyl group ultimately allows the synthesis of (±)-microstegiol.

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/jo102127q at http://pubs.acs.org/doi/abs/10.1021/jo102127q.

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