Srikrishna, A and Reddy, Jagadeeswar T (1998) Stereoselective total synthesis of (+/-)-tochuinyl acetate and (+/-)-dihydrotochuinyl acetates. In: Tetrahedron, 54 (28). pp. 8133-8140.
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Abstract
Details of the first total synthesis of the marine natural product dihydrotochuinyl acetate is described. Cyclopentenone annulation of p-methylacetophenone via a Claisen rearrangement-Wacker oxidation based sequence generated the cyclopentenone 3, a known precursor for the sesquiterpenes cuparene, laurene, alpha-cuparenone and beta-cuparenones. Conversion of the ketone moiety into a carboxylate followed by stereoselective alkylation and reduction transformed the cyclopentenone 3 into the primary alcohol 19. Birch reduction of the alcohol 19 followed by acetylation furnished (+/-)-dihydrotochuinyl acetate, whereas direct acetylation of 19 furnished (+/-)-tochuinyl acetate. (C) 1998 Elsevier Science Ltd. All rights reserved.
Item Type: | Journal Article |
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Publication: | Tetrahedron |
Publisher: | Elsevier Science |
Additional Information: | Copyright of this article belongs to Elsevier Science. |
Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
Date Deposited: | 29 Jun 2011 07:17 |
Last Modified: | 29 Jun 2011 07:17 |
URI: | http://eprints.iisc.ac.in/id/eprint/38670 |
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