Issue 13, 2004
From the journal:

Organic & Biomolecular Chemistry

A one-pot remote allylic hydroxylation and Baeyer–Villiger oxidation of a bicyclo[3.2.0]hept-2-en-6-one by Cunninghamella echinulata NRRL 3655

Ian J. S. Fairlamb,*a   Stephanie Grant,a   Gideon Grogan,*b   David A. Maddrellb  and  Josephine C. Nicholsb  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, UK
E-mail: ijsf1@york.ac.uk
Fax: 44 1904 432516
Tel: 44 1904 434091

b York Structural Biology Laboratory, Department of Chemistry, University of York, Heslington, York, UK
E-mail: gg12@york.ac.uk

Abstract

7-exo-Methyl-7-endo-phenylbicyclo[3.2.0]hept-2-en-6-one 3 undergoes Baeyer–Villiger and allylic oxidation, to yield novel hydroxylactone 8 in good yield by Cunninghamella echinulata NRRL 3655, representing a one step biocatalytic access to a cyclopentanoid scaffold with three chiral centers. Interesting, allylic oxidation occurs with transposition of the double bond.

Graphical abstract: A one-pot remote allylic hydroxylation and Baeyer–Villiger oxidation of a bicyclo[3.2.0]hept-2-en-6-one by Cunninghamella echinulata NRRL 3655

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Article information

DOI
https://doi.org/10.1039/B406016D
Article type
Communication
Submitted
22 Apr 2004
Accepted
26 May 2004
First published
10 Jun 2004

Org. Biomol. Chem., 2004,2, 1831-1833

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A one-pot remote allylic hydroxylation and Baeyer–Villiger oxidation of a bicyclo[3.2.0]hept-2-en-6-one by Cunninghamella echinulata NRRL 3655

I. J. S. Fairlamb, S. Grant, G. Grogan, D. A. Maddrell and J. C. Nichols, Org. Biomol. Chem., 2004, 2, 1831 DOI: 10.1039/B406016D

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