Total Synthesis of (+)‐Yatakemycin | Zendy

Okano Kentaro | Zendy; Tokuyama Hidetoshi | Zendy; Fukuyama Tohru | Zendy

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Total Synthesis of (+)‐Yatakemycin

Author(s) -

Okano Kentaro,

Tokuyama Hidetoshi,

Fukuyama Tohru

Publication year - 2008

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.200700282

Subject(s) - amination , cyclopropane , regioselectivity , ring (chemistry) , yield (engineering) , chemistry , epichlorohydrin , aryl , derivative (finance) , total synthesis , sequence (biology) , stereoselectivity , enantioselective synthesis , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , biochemistry , alkyl , economics , financial economics , metallurgy

A convergent total synthesis of (+)‐yatakemycin was accomplished by a 20‐step sequence in 13 % overall yield. The regioselective ring opening of ( S )‐epichlorohydrin with a 2,6‐dibromophenyllithium derivative enabled us to introduce a chiral carbon center, which was required for the stereoselective construction of the cyclopropane ring. The five aryl–nitrogen bonds in (+)‐yatakemycin were constructed by a mild copper‐mediated aryl amination that utilized the combination of CuI with CsOAc. The efficient and chemoselective debenzylation of aryl benzyl ether with BCl 3 in the presence of pentamethylbenzene was developed. With these new methodologies, the subgram‐scale synthesis of (+)‐yatakemycin was achieved.

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