Stereoselective total synthesis of (±)-tochuinyl acetate and (±)-dihydrotochuinyl acetates

Srikrishna, A. ; Jagadeeswar Reddy, T. (1988) Stereoselective total synthesis of (±)-tochuinyl acetate and (±)-dihydrotochuinyl acetates Tetrahedron, 54 (28). pp. 8133-8140. ISSN 0040-4020

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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, α-cuparenone and β-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.

Item Type:Article
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ID Code:48765
Deposited On:15 Jul 2011 11:23
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