- A practical route to both enantiomers of bicyclo[3.3.0]oct-2-en-7-one and their use for the synthesis of key trisubstituted cyclopentanes
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We describe new methodology for the synthesis of both enantiomers of 7,7-dichlorobicyclo[3.2.0]hep-2-en-6-one and conversion of these compounds into stereochemically defined bicyclo[3.3.0]oct-2-en-7-ones and thence trisubstituted cyclopentanes. These are key intermediates for the synthesis of prostanoids, brefeldin and other cyclopentane-containing natural products.
- Cousin, David,Mann, John
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p. 3534 - 3540
(2008/09/21)
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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.
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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.
- Fairlamb, Ian J S,Grant, Stephanie,Grogan, Gideon,Maddrell, David A,Nichols, Josephine C
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p. 1831 - 1833
(2007/10/03)
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- BIOCATALYTIC PREPARATION OF BICYCLOHEPTANE DERIVATIVES
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Bicyclohept-2-en-6-ols, central building blocks for the synthesis of chiral cyclobutane and -pentane systems, were prepared with up to >99percent e.e. by lipase catalysed resolution of their acetates, butyrates, or isobutyrates.Substituents at C-7 vicinal to the reaction site reduced both enantioselectivity and reaction rate, whereas variation of the acid moiety showed a smaller influence.Among the lipases tested, those from Pseudomonas sp. were shown to be superior to those from Candida cylindracea, Mucor sp. and porcine pancreas.
- Klempier, Norbert,Geymayer, Paul,Stadler, Peter,Faber, Kurt,Griengl, Herfried
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p. 111 - 118
(2007/10/02)
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- Specifically Deuteriated Bicyclohepta-2,6-dienes
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An efficient synthetic route from the dichloroketene/cyclopentadiene adduct to bicyclohepta-2,6-diene has been developed and adapted to prepare deuteriated analogues of this diene labeled specifically at C1-C5, C6, or C7, or any combination of these possibilities.
- Baldwin, John E.,Belfield, Kevin D.
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p. 4772 - 4776
(2007/10/02)
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- Acid-catalyzed rearrangement of cyclobutanols. Syntheses of chrysenes, cyclopentenophenanthrenes, and diarylmethanes
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Acid-catalyzed reactions of 8-aryl or 8,8-diarylbicyclooct-2-en-7-ols lead to tetrahydrophenanthrene derivatives.For example 8-(1-naphthyl)-bicyclooct-2-en-7-ols give substituted chrysenes in methanesulphonic acid.In the case of the homologous 7-aryl or 7,7-diarylbicyclohept-2-en-6-ols a novel transformation of diarylmethanes is observed.A mechanism is proposed which accounts for the product distribution observed in these rearrangements.
- Lee-Ruff, Edward,Hopkinson, Alan C.,Kazarians-Moghaddam, Hira,Gupta, Brij,Katz, Morris
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p. 154 - 159
(2007/10/02)
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