New route to cyclopentene-1-carboxaldehydes by rearrangement of 2,3-epoxycyclohexanols

Magnusson, Göran; Thorén, Svante

doi:10.1021/jo00947a030

Cited by 79 publications

(23 citation statements)

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“…"C-NMR: 18.5 (Mr-C(6)); 22.9 (Me-C(2)); 30.8 (C(4)); 31.0 (C(7)); 39.3 (C(5)); 39.8 (C(6)); 45.5 (C(1)); 51.7 (CHz-C(6)); 116.9 (C(3)); 143.2 (C(2)); 203.7 (CHO). MS: 164 ( I , M"), 131 (43), 120 (52), 105 (76), 93 (loo), 77 (68), 55 (26). 41 (44), 39 (48).…”

Section: 6-dimethyl-6-[(e~-4-me~hylpent~-24-d~en~l]h~cy~~o[3~f]hmentioning

confidence: 99%

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Preparation and Absolute Configuration of (−)‐(E)‐α‐trans‐Bergamotenone

Chapuis

Barthe

Müller

et al. 1998

Helvetica Chimica Acta

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The synthesis, absolute configuration, and olfactive evaluation of (−)‐(E)‐α‐trans‐bergamotenone (= (−)‐(1′S,6′R,E)‐5‐(2′,6′‐dimethylbicyclo[3.1.1]hept‐2′‐en‐6′‐yl)pent‐3‐en‐2‐one; (−)‐1), as well as its homologue (−)‐19 are reperted. The previously arbitrarily attributed absolute configuration of 1 and of (−)‐α‐trans‐bergamotene (= (−)‐(1 S,6R)‐2,6‐dimethyl‐6‐(4‐methylpent‐3‐enyl)bicyclo[3.1. 1]hept‐2‐ene; (−)‐2), together with those of the structurally related aldehydes (−)‐3a,b and alcohols (−)‐4a,b, have been rigorously assigned.

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Section: 6-dimethyl-6-[(e~-4-me~hylpent~-24-d~en~l]h~cy~~o[3~f]hmentioning

confidence: 99%

“…or T H E or acetone [24]; Ce(NH,),(NO,),, MeCN, H,O [25]; LiBr, l-methylpyrolidin-2-one. toluene, 110" [26]; (Et,N)TO,, CH,CI, or MeOH [27]; Pb(OAc),, K,CO,, toluene [28]. This aldehyde, also obtained by partial ozonolysis of (-)-2 (25% mol-equiv.…”

mentioning

confidence: 99%

Preparation and Absolute Configuration of (−)‐(E)‐α‐trans‐Bergamotenone

Chapuis

Barthe

Müller

et al. 1998

Helvetica Chimica Acta

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“…The synthesis commenced with the Luche reduction of cyclohexenone 1 to cyclohexenol 2 ,13 which was directly epoxidized with meta ‐chloroperoxybenzoic acid ( m ‐CPBA) to generate epoxy alcohol 3 14 (see Scheme ). Compound 3 underwent a Ti(O i Pr) 4 mediated regioselective isomerization to produce cis ‐diol 4 in 64 % yield 15.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies of Kinamycin Antibiotics: Stereoselective Synthesis of the Highly Oxygenated D‐Ring and Construction of the ABD‐Ring System of Kinamycins

Ouzouni

Fokas

2013

Eur J Org Chem

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A concise and stereoselective synthesis of the highly oxygenated D‐ring of the kinamycin family of antitumor antibiotics was achieved from commercially available 3‐methyl‐2‐cyclohexen‐1‐one. The key steps included a regioselective isomerization of a cis‐epoxy alcohol, a regioselective reductive ring opening of a benzylidene ketal, and a stereoselective α‐hydroxy‐directed ketone reduction. The Ullmann coupling between a bromonaphthaldehyde AB‐ring fragment and an α‐iodocyclohexenone, which is a versatile D‐ring precursor, effected the construction of the functionalized ABD‐ring system that may provide access to kinamycin F and its structural analogues.

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“…-IR. (CH2C12): 2930, 2890, 2810, 2760, 1617, 1503, 1455, 1362, 1345, 1235, 1065, 1030, 131 (29), 104 (47). (22).…”

Section: Experimental Partmentioning

confidence: 99%

ChemInform Abstract: HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF (.+‐.)‐CHELIDONINE AND OF (.+‐.)‐NORCHELIDONINE BY AN INTRAMOLECULAR O‐QUINODIMETHANE/NITROSTYRENE‐CYCLOADDITION

Oppolzer¹,

Robbiani²

1984

Chemischer Informationsdienst

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New route to cyclopentene-1-carboxaldehydes by rearrangement of 2,3-epoxycyclohexanols

Cited by 79 publications

References 1 publication

Preparation and Absolute Configuration of (−)‐(E)‐α‐trans‐Bergamotenone

Preparation and Absolute Configuration of (−)‐(E)‐α‐trans‐Bergamotenone

Synthetic Studies of Kinamycin Antibiotics: Stereoselective Synthesis of the Highly Oxygenated D‐Ring and Construction of the ABD‐Ring System of Kinamycins

ChemInform Abstract: HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF (.+‐.)‐CHELIDONINE AND OF (.+‐.)‐NORCHELIDONINE BY AN INTRAMOLECULAR O‐QUINODIMETHANE/NITROSTYRENE‐CYCLOADDITION

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