2006
DOI: 10.1021/np0502847
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A New Route toward 7-Oxo-13-hydroxy-8,11,13-podocarpatrienes from Labdane Diterpenes

Abstract: Trinorlabdane 1,5-diketones (7, 10a,b, 13a,b), which are easily prepared from labdane diterpenes, are directly converted into the corresponding 7-oxo-13-hydroxy-8,11,13-podocarpatrienes, immediate precursors of bioactive compounds, under basic treatment. Utilizing this strategy, the first enantiospecific synthesis of 13-hydroxy-8,11,13-podocarpatriene (20), a constituent of Taiwania cryptomerioides, was achieved starting from (-)-sclareol (5) after a seven-step sequence in 55% overall yield.Podocarpane diterpe… Show more

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Cited by 12 publications
(4 citation statements)
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“…Recently, a new route to compound 1 in seven steps via β-enone 7 from (+)-sclareol has been reported. 27 The key step involves the intramolecular aldol condensation of a trinorlabdane 1,5-diketone, aromatisation of the resulting β-enone, and benzylic oxidation. Previously Nakano et al 28 reported the synthesis of β-enone 7 from (+)-manool 4 in three steps.…”
Section: Resultsmentioning
confidence: 99%
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“…Recently, a new route to compound 1 in seven steps via β-enone 7 from (+)-sclareol has been reported. 27 The key step involves the intramolecular aldol condensation of a trinorlabdane 1,5-diketone, aromatisation of the resulting β-enone, and benzylic oxidation. Previously Nakano et al 28 reported the synthesis of β-enone 7 from (+)-manool 4 in three steps.…”
Section: Resultsmentioning
confidence: 99%
“…29 Ozonolysis of ketone 5 afforded diketone 6. 27,28 Intramolecular aldol condensation utilising a dilute solution of H 2 SO 4 afford the desired compound 7 in 80% yield. 30,31 To synthesise compound 1, we first tried aromatisation of β-enone 7 with DDQ and SeO 2 .…”
Section: Resultsmentioning
confidence: 99%
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“…Several natural podocarpanes with an aromatic ring C have been reported to exhibit various biological properties such as antitumoural, [1][2][3][4][5] antifungal, 6 5-lipoxygenase 7,8 and anti-hepatitis C viral (anti-HCV) 9 activities. Furthermore, different synthetic compounds related to podocarpanes with aromatic ring C have shown modulation of large-conductance calcium-activated potassium channels (BK channels), 10,11 antiplasmodial, 12 antiproliferative, 13 anti-inflammatory 14 and gastroprotective 15 activity.…”
mentioning
confidence: 99%