A rearranged labdane: Salmantic acid from Cistus laurifolius

Teresa, J. De Pascual; Urones, Julio G.; Marcos, Isidro S.; Bermejo, Francisco; Basabe, P.

doi:10.1016/s0031-9422(00)97696-9

Cited by 21 publications

(16 citation statements)

References 1 publication

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“…85,98 In many of these plants that contain halimanes, labdanes have also been isolated and in other plants they coexist with clerodanes. For example, in a Cistaceae such as Halimium viscosum ent-halimanes and labdanes coexist, 17,26,28,99,100 in Cistus laurifolius labdanes, ent-labdanes, cis-clerodanes and ent-halimanes have been isolated, [101][102][103][104] and in plants of genus Croton 44,105-107 (Euphorbiaceae) labdanes, halimanes and clerodanes coexist. In Haplopappus paucidentatus 25 and Nardophyllum lanatum 19 (Compositae) labdanes, halimanes and clerodanes coexist.…”

Section: Enzymatic and Genetic Experimental Studiesmentioning

confidence: 99%

“…Their structures were spectroscopically determined and their absolute congurations assigned by chemical correlation by comparison with rearranged products of labdanolic, populifolic or ent-halimic acid. 102,168 The ve compounds of this type are functionalized at C3. Salmantic acid (170), its methyl ester (171) and salmantidiol (172) have the side chain saturated, while leucasperone A (173) and leucasperone B (174), isolated from Leucas aspera, 169 show a double bond at C14 and have oxygenated functions at C11 and C13.…”

Section: Halim-5(10)-enes Groupmentioning

confidence: 99%

“…Reaction of 292 with 3-furyllithium followed by oxidation gave the key intermediate 300 (36%, global). Chettaphanin II (102) was obtained by reaction of 300 in acidic media (92%) and chettaphanin I (38) was synthesized from 300 in two steps: epoxidation followed by reaction in acidic media (28%, two steps). 5.1.3.…”

Section: Ent-halimic Acid As Precursor Of Biologically Active Compounmentioning

confidence: 99%

“…8-epi-ent-Halim-5(10)-enes. The rst known halim-5(10)-enes appear within this series: salmantic acid (170), its methyl ester(171) and salmantidiol(172), isolated from Cistus laurifolius102…”

mentioning

confidence: 99%

“…Chettaphanins synthesis. An efficient synthesis of the rst known ent-halimanes, chettaphanin I (38) and II(102), has been achieved from ent-halimic acid methyl ester 39 (Scheme 13). The absolute conguration of the natural products was established by nOe and X-ray analysis of chettaphanin II (102) 109,209.…”

mentioning

confidence: 99%

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Halimane diterpenoids: sources, structures, nomenclature and biological activities

et al. 2018

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Covering: 1970 to 2017 Diterpenes with a halimane skeleton constitute a small group of natural products that can be biogenetically considered as being between labdane and clerodane diterpenoids. Some of these compounds show biological activities, such as antitumour, mosquito repellency, germination inhibition and antimicrobial, as well as being biomarkers for tuberculosis. To the best of our knowledge, there are no reviews on these compounds. In this review, halimane skeleton diterpenoids are classified according to their biogenetic origin, characterization and/or the enzymes involved in their biosynthesis. Herein, a review of their synthesis or synthetic approaches is communicated.

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