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Volumn 21, Issue 12, 2015, Pages 4529-4533

Total synthesis of an exceptional brominated 4-pyrone derivative of algal origin: An exercise in gold catalysis and alkyne

Author keywords

Alkyne metathesis; Biosynthesis; Gold; Heterocycles; Molybdenum; Natural products

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; CATALYSIS; HYDROCARBONS; MOLYBDENUM; SCAFFOLDS; GOLD; METABOLITES;

EID: 84924093623     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500437     Document Type: Article
Times cited : (47)

References (57)
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    • 2 (93% inhibition at 4.4 mm concentration) whereas 4 is a feeding deterrent for herbivorous gastropods and sea urchins and therefore likely plays a role for the chemical defense of the producing algae, see
    • Compound 1 inhibits phospholipase A2 (93% inhibition at 4.4 mm concentration) whereas 4 is a feeding deterrent for herbivorous gastropods and sea urchins and therefore likely plays a role for the chemical defense of the producing algae, see: a) A. M. S. Mayer, V. J. Paul, W. Fenical, J. N. Norris, M. S. de Carvalho, R. S. Jacobs, Hydrobiologia 1993, 260 - 261, 521 -529;
    • (1993) Hydrobiologia , vol.260-261 , pp. 521-529
    • Mayer, A.M.S.1    Paul, V.J.2    Fenical, W.3    Norris, J.N.4    De Carvalho, M.S.5    Jacobs, R.S.6
  • 9
    • 84924098079 scopus 로고    scopus 로고
    • Only the bromination of 4-pyrones devoid of additional unsaturations is known, see
    • Only the bromination of 4-pyrones devoid of additional unsaturations is known, see:
  • 15
    • 84924175336 scopus 로고    scopus 로고
    • Only 2-methoxy-4-pyrones are reasonably common in nature; for illustrative total syntheses of such compounds, see the following and literature cited therein
    • Only 2-methoxy-4-pyrones are reasonably common in nature; for illustrative total syntheses of such compounds, see the following and literature cited therein:
  • 21
    • 84924178695 scopus 로고    scopus 로고
    • This reaction enabled the total synthesis of neurymenolide A; although this compound is a 2-pyrone with a cyclophane scaffold, it is arguably the closest relative of 1-6 currently known
    • This reaction enabled the total synthesis of neurymenolide A; although this compound is a 2-pyrone with a cyclophane scaffold, it is arguably the closest relative of 1-6 currently known.
  • 27
  • 29
    • 84924124419 scopus 로고    scopus 로고
    • [12]
    • [12]
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    • 84924200347 scopus 로고    scopus 로고
    • The corresponding allylic iodide underwent quantitative isomerization to the E-configured substitution product under otherwise identical conditions
    • The corresponding allylic iodide underwent quantitative isomerization to the E-configured substitution product under otherwise identical conditions.
  • 39
    • 84924207730 scopus 로고    scopus 로고
    • Details will be reported in a future full paper
    • Details will be reported in a future full paper.
  • 41
    • 78149425384 scopus 로고    scopus 로고
    • Protodeauration likely has to outperform diauration of the reactive intermediates
    • Protodeauration likely has to outperform diauration of the reactive intermediates, see: a) G.Seidel, C. W.Lehmann, A. F rstner, Angew. Chem. Int. Ed. 2010, 49, 8466 -8470;
    • (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 8466-8470
    • Seidel, G.1    Lehmann, C.W.2    F rstner, A.3
  • 45
    • 84924209424 scopus 로고    scopus 로고
    • For applications of RCAM to other natural products of polyacetate origin
    • For applications of RCAM to other natural products of polyacetate origin, see:
  • 48
    • 85009713288 scopus 로고    scopus 로고
    • H = 4.14 ppm in ref. [2]; for details see the Supporting Information
    • H = 4.14 ppm in ref. [2]; for details see the Supporting Information.
  • 49
    • 84924144683 scopus 로고    scopus 로고
    • Because theαD of 1 has not been reported, the absolute configuration cannot be defined
    • D of 1 has not been reported, the absolute configuration cannot be defined.
  • 50
    • 84924143970 scopus 로고    scopus 로고
    • For the sake of brevity, the -OH group in 16 was inverted and the resulting alcohol 20-epi-16 advanced to anti-1; for details, see the Supporting Information
    • For the sake of brevity, the -OH group in 16 was inverted and the resulting alcohol 20-epi-16 advanced to anti-1; for details, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.