1993
DOI: 10.1021/np50102a016
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Studies on the Synthesis of Scoparic Acid A and Related Labdane Diterpenoids. Synthesis of (E)-6β-Hydroxylabda-8-(17),13-dien-15-oic Acid

Abstract: ~STRACT.-A general strategy for a successful approach to labdanes of the type 3-5 is described. This methodology, which makes use of the known Eschenmoser fragmentation of 9, 1,3-oxidative rearrangement of allylic tertiary alcohol 14, and photochemical double bond isomerization ofallylic acetate 17 as key synthetic steps, is used to prepare optically pure labdane 5 from readily available (+)-podocarpenone 8.

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Cited by 10 publications
(3 citation statements)
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“…(−)- ent -6-β-Hydroxycopalic acid (7) was obtained as a colorless oil: [α] D 25 −25.3 ( c 0.43, CHCl 3 ); 1 H NMR and 13 C NMR data were consistent with those previously reported and authentic sample , ; ESI-MS, m / z 321 [M + H] + .…”
Section: Methodssupporting
confidence: 78%
See 1 more Smart Citation
“…(−)- ent -6-β-Hydroxycopalic acid (7) was obtained as a colorless oil: [α] D 25 −25.3 ( c 0.43, CHCl 3 ); 1 H NMR and 13 C NMR data were consistent with those previously reported and authentic sample , ; ESI-MS, m / z 321 [M + H] + .…”
Section: Methodssupporting
confidence: 78%
“…Together with lignans 1 and 2, (-)-copalic acid ( 5), (-)fargesin ( 6), (-)-ent-6-β-hydroxy-copalic acid (7), (8R,8′R,9R)and (8R,8′R,9S)-cubebins ( 8), (-)-phillygenin (9), and 2-oxokolavenic acid (10) were isolated from the hexane extract of the leaves by partition and chromatographic procedures. The structures of these compounds were identified by comparison of their spectroscopic data (ESI-MS, IR, 1 H and 13 C NMR) and optical activities (R D ) with those reported in the literature (21,22,(24)(25)(26)(27)(28)(29)(30)(31)(32). Although furofuran lignans have been known for some time, the determination of their configurations is still a subject of controversy (26,27).…”
Section: Resultsmentioning
confidence: 99%
“…Workup as in the case of 1 gave a residue which was purified by cc over Si gel. The fractions eluted with hexane-EtOAc (8:2) afforded diacetate 7 as a white solid which was recrystallized from CHCl3/hexane to yield white prisms (97 mg, 73%), mp 128-130°; Arteag-9-en-7a,8$-diol-1 -one 7-monoacetate [8],-A solution of endiolone 3 (83 mg) in pyridine (1 ml) was treated with Ac20 (1 ml). The reaction mixture was heated on a steam bath for 90 min, poured over ice-H20, and extracted with EtOAc.…”
Section: T H I S C O N T E N T Imentioning
confidence: 99%