Title of article :
Total synthesis of aspergillide B and structural discrepancy of aspergillide A
Author/Authors :
Hande، نويسنده , , Sudhir M. and Uenishi، نويسنده , , Jun’ichi، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2009
Pages :
4
From page :
189
To page :
192
Abstract :
Fourteen-membered cytotoxic macrolides 1 and 2 were synthesized from alcohol 10 in 15 steps utilizing stereospecific Pd(II)-catalyzed cyclization of ζ-hydroxy chiral allylic alcohol 7. Aspergillides A and B were isolated from marine fungus, and their structures were proposed as 1 and 2, respectively. The synthetic 1 was not matched with aspergillide A but matched with aspergillide B. The chiral center at C-13 position of aspergillide B was revised to be (S)-configuration. The key steps of the stereoselective synthesis include the Sharpless asymmetric dihydroxylation, cross-metathesis, stereospecific construction of tetrahydropyran ring of 16 using PdII catalyst, and the Yamaguchi macrolactonization.
Journal title :
Tetrahedron Letters
Serial Year :
2009
Journal title :
Tetrahedron Letters
Record number :
1862244
Link To Document :
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