2001
DOI: 10.1590/s0103-50532001000200005
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A novel dihydroxy nor-guaiane sesquiterpene: synthesis and crystal structure analysis

Abstract: A epoxidação (H 2 O 2 , NaOH) de uma cicloeptenona-acetonilada forneceu um sesquiterpeno norguaiano bis-hidroxilado, através de uma seqüência inesperada de reações. Análise espectroscópica deste produto permitiu propor uma estrutura incluindo os grupos substituintes, porém a determinação tridimensional completa foi realizada por uma análise de difração de raio-X.The epoxidation (H 2 O 2 , NaOH) of an acetonyl-cycloheptenone derived from (R)-(-)-carvone gives a dihydroxy-nor-guaiane sesquiterpene by way of an i… Show more

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Cited by 9 publications
(4 citation statements)
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“…The occurrence of substances with this type of skeleton is not common in the Lauraceae family 15 . The occurrence of substances with this type of skeleton is not common in the Lauraceae family 15 .…”
Section: Resultsmentioning
confidence: 99%
“…The occurrence of substances with this type of skeleton is not common in the Lauraceae family 15 . The occurrence of substances with this type of skeleton is not common in the Lauraceae family 15 .…”
Section: Resultsmentioning
confidence: 99%
“…This has provoked studies on the synthesis of suitable seven‐membered ring intermediates, frequently by expansion of readily available cyclohexane starting materials . Our approach is to utilise para ‐menthane monoterpenes, because of their availability, price, enantiomeric purity and occurrence in both series, and diverse functionality …”
Section: Introductionmentioning
confidence: 99%
“…Our interest in their synthesis has led us to develop methods for the transformation of para-menthane monoterpenes into single isomer cycloheptenones, [2][3][4] and then by pent-annelation 5,6 into the required complete carbon skeleton. Scheme 1 outlines our synthetic strategy which involves two quite different routes for the ring expansion, by cyclopropanation and central sigma bond cleavage 2,3 or nucleophilic addition and rearrangement.…”
Section: Introductionmentioning
confidence: 99%
“…Scheme 1 outlines our synthetic strategy which involves two quite different routes for the ring expansion, by cyclopropanation and central sigma bond cleavage 2,3 or nucleophilic addition and rearrangement. 4 The intermediate cycloheptenone can then by pent-annelated by more classical ionic reactions (allylation, Wacker oxidation and intramolecular aldol reaction) 5 or by the ring closing metathesis 6 of a suitable neighboring allyl-vinyl derivative.…”
Section: Introductionmentioning
confidence: 99%