A concise synthesis of chiral 2-methyl chroman-4-ones: stereo selective build-up of the chromanol moiety of anti-HIV agent calanolide A

Rama Rao, A. V. ; Gaitonde, A. S. ; Prakash, K. R. C. ; Prahlada Rao, S. (1994) A concise synthesis of chiral 2-methyl chroman-4-ones: stereo selective build-up of the chromanol moiety of anti-HIV agent calanolide A Tetrahedron Letters, 35 (34). pp. 6347-6350. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)73429-0

Abstract

Inter- and Intramolecular Houben-Hoesch reactions have been used for the first time for the enantioselective synthesis of both the antipodes of 5,7-dimethoxy-2-methyl chroman-4-one. (R)-7-Methoxy-2-methyl chroman-4-one has been diastereoselectively elaborated to the dimethylchromanol moiety of calanolide A.

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