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Communication | Special issue | Vol 47, No. 1, 1998, pp.59-64
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)2
A Stereoselective Synthesis of 4-O-Methyl- 13-desacetyl-12,13-di-O-benzylcarzinophilin

Masaru Hashimoto and Shiro Terashima*

*Sagami Central Research Center, Nishi-Ohnuma, Sagamihara, Kanagawa 229-0012, Japan


The title synthesis was achieved by the synthetic scheme featuring the following four key steps: i) coupling of the methyl thioimidate with the 2-oxazolin-5-one (5+613), ii) construction of the C17-C21 functionality by the use of Sharpless asymmetric dihydroxylation and subsequent manipulation of the functional groups (13→→→21), iii) activation of the 4-(pyrrolidin-2-ylidene)-2-oxazolin-5-one system by introducing an Alloc group into N9 position and subsequent ring opening with the L-threonine derivative (21+726), and iv) construction of the characteristic 2-methylidene-1-azabicyclo[3.1.0]hexane system with TBAF (302).