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Stereoselective total synthesis of (±)-tochuinyl acetate and (±)-dihydrotochuinyl acetates
- Source :
- Tetrahedron. 54:8133-8140
- Publication Year :
- 1998
- Publisher :
- Elsevier BV, 1998.
-
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, 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.
Details
- ISSN :
- 00404020
- Volume :
- 54
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........a9102b51c8f9441449e25a6de44c10ce