A chemoenzymatic synthesis of the carbobicyclic core associated with CP-225,917 and CP-263,114 (phomoidrides A and B)

Banwell, Martin; McRae, Kenneth; Willis, Anthony

A chemoenzymatic synthesis of the carbobicyclic core associated with CP-225,917 and CP-263,114 (phomoidrides A and B)

Date

2001

Authors

Banwell, Martin

McRae, Kenneth

Willis, Anthony

Publisher

Royal Society of Chemistry

Abstract

The bromobenzene-derived and enantiopure cis-1,2-dihydrocatechol 3 has been converted, via a reaction sequence involving Diels-Alder cycloaddition, anionic oxy-Cope rearrangement and Wolff ring-contraction steps, into compound 4 and epimer 24, which embody key structural elements associated with the nonadride-type natural products CP-225,917 (1) and CP-263,114 (2).

Keywords

Keywords: Addition reactions; Alcohols; Bromine compounds; Carboxylic acids; Enzymes; Hydrogen bonds; Hydrolysis; Hydroxylation; Molecular structure; Nuclear magnetic resonance spectroscopy; Stereochemistry; X ray crystallography; Chemoenzymatic synthesis; Synthesi

URI

http://hdl.handle.net/1885/94182

Collections

ANU Research Publications

Source

Journal of the Chemical Society, Perkin Transactions 1

Type

Journal article

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A chemoenzymatic synthesis of the carbobicyclic core associated with CP-225,917 and CP-263,114 (phomoidrides A and B)

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