First enantioselective synthesis and determination of the absolute configuration of natural (+)-dehydro-β-monocyclonerolidol

Palombo, Elie; Audran, Gérard; Monti, H.

doi:10.1016/s0040-4039(03)01562-4

Cited by 8 publications

(5 citation statements)

References 7 publications

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“…The 1 H- and 13 C-NMR spectroscopic data of the synthesized compound 6 were superimposable with those reported for the synthetic [18,19] and the natural [8] sesquiterpene, whereas the measured optical rotation value, [α] 20 D = −34.4 ( c 1.1, CH 2 Cl 2 ), show comparable value and opposite sign of the naturally occurring ( S )-pallescensone, [α] 20 D = +36 ( c 1.0, CHCl 3 ).…”

Section: Resultssupporting

confidence: 69%

“…The proposed synthesis of compounds 2 , 4 , and 5 compare favorably over the previously reported stereoselective methods [11,15,18,19] since the overall yields are higher, the approach is operationally simple, and it afforded the target compounds in high stereoisomeric purity.…”

Section: Resultsmentioning

confidence: 79%

“…Almost immediately after their identification, both the chemical structure and the absolute configuration of the pallescensin-1 ( 2 ) and of the pallescensin-2 ( 4 ) were confirmed by chemical synthesis [11]. Thereafter, several new synthetic approaches [12,13,14,15,16,17,18,19] provided compounds 2 , 5 , and 6 both in racemic and in enantioenriched forms. Curiously, isomicrocionin-3 ( 3 ) has not been prepared yet, whereas pallescensis-2 ( 4 ) has been synthesized only in racemic form.…”

Section: Introductionmentioning

confidence: 99%

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A General Strategy for the Stereoselective Synthesis of the Furanosesquiterpenes Structurally Related to Pallescensins 1–2

Serra

2019

Marine Drugs

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Here, we describe a general stereoselective synthesis of the marine furanosesquiterpenes structurally related to pallescensins 1–2. The stereoisomeric forms of the pallescensin 1, pallescensin 2, and dihydropallescensin 2 were obtained in high chemical and isomeric purity, whereas isomicrocionin-3 was synthesized for the first time. The sesquiterpene framework was built up by means of the coupling of the C10 cyclogeranyl moiety with the C5 3-(methylene)furan moiety. The key steps of our synthetic procedure are the stereoselective synthesis of four cyclogeraniol isomers, their conversion into the corresponding cyclogeranylsulfonylbenzene derivatives, their alkylation with 3-(chloromethyl)furan, and the final reductive cleavage of the phenylsulfonyl functional group to afford the whole sesquiterpene framework. The enantioselective synthesis of the α-, 3,4-dehydro-γ- and γ-cyclogeraniol isomers was performed using both a lipase-mediated resolution procedure and different regioselective chemical transformations.

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Section: Resultssupporting

confidence: 69%

Section: Resultsmentioning

confidence: 79%

Section: Introductionmentioning

confidence: 99%

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A General Strategy for the Stereoselective Synthesis of the Furanosesquiterpenes Structurally Related to Pallescensins 1–2

Serra

2019

Marine Drugs

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“…5). Like previously, our enantioselective synthesis of (+)-(6) was reported starting from karahana lactone for the introduction and determination of the absolute stereochemistry [17]. Like previously, our enantioselective synthesis of (+)-(6) was reported starting from karahana lactone for the introduction and determination of the absolute stereochemistry [17].…”

Section: Enantioselective Synthesis Of Dehydro-β -Monocyclonerolidol supporting

confidence: 53%

Lipases-Promoted Enantioselective Syntheses of Monocyclic Natural Products

Monti¹,

Audran²

2005

MROC

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“…Enantioselective Synthesis. We chose as our starting point the known Karahana lactone 18 which was readily transformed in four steps into the chiral aldehyde (+)- 3 (Scheme ) .…”

Section: Resultsmentioning

confidence: 99%