Anthracyclinones synthesis

Anthracyclinone synthesis. Wulf and Xu1 have reported a high-yield formal synthesis of 11-deoxydaunomycinone (5) in which the first step is a benzannelation of the chromium carbene 1 with the acetylene 2 to provide the naphthol 3, which is not isolated but treated with TFA to induce cleavage of the /-butyl ester and to... 

Oxygenation of a silane. In the course of an anthracyclinone synthesis, Vedejs and Pribish2 found that a benzylic trimethylsilane can be converted into a hydroxyl group by reaction with TASF in the presence of oxygen and trimethyl phosphite (2 — 3,95% yield). The conversion is considered to involve formation of a benzylic... 

Asymmetric reduction of a,fi-enon s. This combination of reagents (1 1) in conjunction with N-cthylaniline (2 equivalents) reduces alkyl aryl ketones to alcohols with high stereoselectivity.1 Under these conditions 2,/1-unsaturated ketones arc reduced to optically active (S)-allylic alcohols. Optical yields of 80 98% have been reported for open-chain enones. Reduction of cyclic enones is somewhat less efficient. The method was used to reduce 1 to 2, which has been used as an intermediate in an anthracyclinone synthesis.2... 

It was stated in a Tetrahedron Report that the Marschalk reaction is "By far the most important reaction for anthracyclinone synthesis using anthraquinones as starting materials."... 

A chiral complex of (1), L1A1H4, and A/-ethylaniline (molar ratio, 1 1 2) reduces aryl alkyl ketones to optically active alcohols in high ee. a, -Unsaturated ketones are reduced enantioselectively to afford optically active (S)-allylic alcohols with 80-98% ee. An intermediate in an anthracyclinone synthesis is prepared in 92% ee by the enantioselective reduction of a cyclic a,p-unsaturated ketone (eq 2). ... 

Anthracene, 9,10-dihydro-9,9-dimethyl-as antidepressant, 1, 169 Anthracene, 1,4,5,8,9-pentamethyl-synthesis, 2, 537 Anthracyclinones synthesis, 1, 414, 4, 700 Anthramycin synthesis, 7, 614 Anthranil, 3-acyl-rearrangement, 5, 93 Anthranil, 3-aiyl-acridones from, 2, 93 thermolysis, 5, 91 Anthranil, 3-(imidazol-2-yl)-rearrangement, 5, 433 Anthranil, 6-nitro-reactions... 

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