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Synlett 1998; 1998(10): 1045-1046
DOI: 10.1055/s-1998-1892
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An Asymmetric Synthetic Route to (+)-Lactacystin

Sung Ho Kang* , Hyuk-Sang Jun, Joo-Hack Youn
  • *Department of Chemistry, Korea Advanced Institute of Science and Technology, Taejon 305-701, Korea; Fax 82(42)8 69 28 10; E-mail: shkang@kaist.ac.kr
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Publication Date:
31 December 2000 (online)

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Trihydroxy pyrrolidinone 16, a key intermediate to (+)-lactacystin 1, has been stereoselectively synthesized via the highly diastereoselective crotylboration of aldehyde 5 and intramolecular mercurioamidation of allylic trichloroacetimidate 12 to introduce the three requisite contiguous chiral centers of methyl, hydroxy and amino substituents.

(+)-lactacystin - neurotrophic activity - crotylboration - trichloroacetimidate - mercurioamidation