Perovskone: a triterpene with a novel carbon skeleton from Perovskia abrotanoides

Parvez, Aslam; Choudhary, M. Iqbal; Akhter, Farzana; Noorwala, Mushtaq; Mohammad, Faryal Vali; Hasan, Nahid; Zamir, Talat; Ahmad, Viqar Uddin

doi:10.1021/jo00042a006

Cited by 45 publications

(41 citation statements)

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“…Initially, it was thought that 126 was constructed from an icetexone precursor 127 and geranyl pyrophosphate (Scheme 26). [63] A [4+2] cycloaddition route from 128 and trans-b-ocimene 129 was later proposed and this concept was used to complete a biomimetic total synthesis (Scheme 27). [64] …”

Section: Methodsmentioning

confidence: 99%

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Chemistry and Biology of Biosynthetic Diels–Alder Reactions

2003

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Nature's repertoire of biosynthetic transformations has recently been recognized to include the Diels-Alder cycloaddition reaction. Evidence now exists that there are enzymes that mediate the Diels-Alder reaction in secondary metabolic biosynthetic pathways. 2002 marked the 100th anniversary of Alder's birth and 75 years since the discovery of the Diels-Alder reaction. It would appear that living systems discovered and made use of this ubiquitously useful ring-forming reaction eons ago for the construction of complex natural products. In this Review an overview is given of all of the known classes of natural products (polyketides, isoprenoids, phenylpropanoids, alkaloids) that have been speculated to arise by a biological Diels-Alder reaction.

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Section: Methodsmentioning

confidence: 99%

“…Early biosynthetic proposal for perovskone (126). [63] Scheme 27. Biomimetic total synthesis of perovskone (126).…”

Section: Heliocidesmentioning

confidence: 99%

Chemistry and Biology of Biosynthetic Diels–Alder Reactions

2003

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“…In 1994 we achieved a 16-step synthesis of the triterpene (±)-perovskone (1) [37] that featured a cascade process in which three rings and five stereocenters of the product were created in a single operation (Scheme 2) [38].…”

Section: Open Accessmentioning

confidence: 99%

Diels-Alder Reactions of 12-Hydroxy-9(10®20)-5aH-abeo-abieta-1(10),8(9),12(13)-triene-11,14-dione

et al. 2013

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12-Hydroxy-9(10→20)-5aH-abeo-abieta-1(10),8(9),12(13)-triene-11,14-dione (quinone 2) served as the dienophile in numerous intermolecular Diels-Alder reactions. These cycloadditions were conducted either thermally (including microwave heating) or with Lewis acid activation. While most dienes reacted with quinone 2 in good chemical yield, others were incompatible under the experimental conditions used.

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“…The mixture was stirred at 0°C for 1 h, and then at room temperature overnight. It was diluted with diethyl ether (10 mL) and saturated NH 4 Cl solution (10 mL). After separation of the layers, the aqueous phase was washed with diethyl ether (3 × 7 mL).…”

Section: -(3-isopropyl-245-trimethoxyphenyl)ethanol (17)mentioning

confidence: 99%

“…[1,2] The plant belongs to the family of Lamiaceae whose members have been the source of several antitumor compounds. Some years ago, the group of Ahmad isolated and characterized a range of interesting polycyclic triterpenes from Salvia bucharica, among them salvadione A [3] (1), perovskone [4] (2), and isoperadione [5] (3) (Figure 1). According to a biosynthetic proposal by Ahmad, [2] these compounds originate from the tricyclic compound 6 and fragments derived from geranyl diphosphate (4).…”

Section: Introductionmentioning

confidence: 99%