AN ENANTIOSELECTIVE SYNTHESIS OF THE RESORCYLIC ACID LACTONE L-783,277 VIA ADDITION OF AN ACETYLIDE ANION TO A TETHERED WEINREB AMIDE

作者：Lin Andrew^*; Willis Anthony C; Banwell Martin G

来源：Heterocycles, 2010, 82(1): 313-318.

DOI：10.3987/COM-10-S(E)67

• Acetylide Anion
• L-783,277
• Macrolactonization
• Resorcylic Acid Lactone
• Weinreb Amide

Treatment of the terminal acetylene 12, readily obtained from the previously reported acid 10, with LiHMDS resulted in a novel macrocyclization reaction to give the cycloalkyne 13. Subjection of compound 13 to hydrogenation under Lindlar-type conditions afforded the Z-configured enone 14 that could be converted into the resorcylic acid lactone 4 upon treatment with BCl3 in CH2Cl2 at -78 degrees C.

• 出版日期2010-12-31