Refereed journal article or data article (A1)
Synthesis of naturally occurring (+)-osmundalactone and 4-epi-(+)-osmundalactone from triacetyl-O-D-glucal
List of Authors: Kotammagari TK, Gonnade RG, Bhattacharya AK
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Publication year: 2015
Journal: Tetrahedron Letters
Journal name in source: TETRAHEDRON LETTERS
Journal acronym: TETRAHEDRON LETT
Volume number: 56
Issue number: 21
Start page: 2783
End page: 2786
Number of pages: 4
ISSN: 0040-4039
DOI: http://dx.doi.org/10.1016/j.tetlet.2015.04.038
Abstract
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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