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; J C  Nichols

doi:10.1039/b406016d

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, J C Nichols

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1831-1833
Number of pages	3
Journal	Organic and Biomolecular Chemistry
Volume	2
Issue number	13
DOIs	https://doi.org/10.1039/b406016d
Publication status	Published - 2004

Keywords

CHEMOENZYMATIC SYNTHESIS

Access to Document

10.1039/b406016d

Cite this

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title = "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",

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.",

keywords = "CHEMOENZYMATIC SYNTHESIS",

author = "Fairlamb, {I J S} and S Grant and G Grogan and Maddrell, {D A} and Nichols, {J C}",

year = "2004",

doi = "10.1039/b406016d",

language = "English",

volume = "2",

pages = "1831--1833",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "The Royal Society of Chemistry",

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T1 - 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

AU - Fairlamb, I J S

AU - Grant, S

AU - Grogan, G

AU - Maddrell, D A

AU - Nichols, J C

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

KW - CHEMOENZYMATIC SYNTHESIS

U2 - 10.1039/b406016d

DO - 10.1039/b406016d

M3 - Article

SN - 1477-0520

VL - 2

SP - 1831

EP - 1833

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 13

ER -