Refereed journal article or data article (A1)

Synthesis of naturally occurring (+)-osmundalactone and 4-epi-(+)-osmundalactone from triacetyl-O-D-glucal




List of AuthorsKotammagari TK, Gonnade RG, Bhattacharya AK

PublisherPERGAMON-ELSEVIER SCIENCE LTD

Publication year2015

JournalTetrahedron Letters

Journal name in sourceTETRAHEDRON LETTERS

Journal acronymTETRAHEDRON LETT

Volume number56

Issue number21

Start page2783

End page2786

Number of pages4

ISSN0040-4039

DOIhttp://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.


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