Vertaisarvioitu alkuperäisartikkeli tai data-artikkeli tieteellisessä aikakauslehdessä (A1)
Synthesis of naturally occurring (+)-osmundalactone and 4-epi-(+)-osmundalactone from triacetyl-O-D-glucal
Julkaisun tekijät: Kotammagari TK, Gonnade RG, Bhattacharya AK
Kustantaja: PERGAMON-ELSEVIER SCIENCE LTD
Julkaisuvuosi: 2015
Journal: Tetrahedron Letters
Tietokannassa oleva lehden nimi: TETRAHEDRON LETTERS
Lehden akronyymi: TETRAHEDRON LETT
Volyymi: 56
Julkaisunumero: 21
Aloitussivu: 2783
Lopetussivun numero: 2786
Sivujen määrä: 4
ISSN: 0040-4039
DOI: http://dx.doi.org/10.1016/j.tetlet.2015.04.038
Tiivistelmä
An efficient total synthesis of (+)-osmundalactone 1 has been achieved starting from readily available triacetyl-O-D-glucal 6 employing Ferrier rearrangement and Jones oxidation as key steps. Also, synthesis of 4-epi-(+)-osmundalactone 2 was accomplished from the common key intermediate 9. The absolute stereochemistry of (+)-osmundalactone 1 and a precursor of 4-epi-(+)-osmundalactone 2 have been established by single crystal X-ray analysis. The overall yield of compound 1 and 2 from triacetyl-O-D-glucal 6 is 13% and 8%, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
An efficient total synthesis of (+)-osmundalactone 1 has been achieved starting from readily available triacetyl-O-D-glucal 6 employing Ferrier rearrangement and Jones oxidation as key steps. Also, synthesis of 4-epi-(+)-osmundalactone 2 was accomplished from the common key intermediate 9. The absolute stereochemistry of (+)-osmundalactone 1 and a precursor of 4-epi-(+)-osmundalactone 2 have been established by single crystal X-ray analysis. The overall yield of compound 1 and 2 from triacetyl-O-D-glucal 6 is 13% and 8%, respectively. (C) 2015 Elsevier Ltd. All rights reserved.
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