Synthesis of ovalicin starting from D-mannose |
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Authors: | Takahashi Shunya Hishinuma Nobuyuki Koshino Hiroyuki Nakata Tadashi |
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Institution: | RIKEN (The Institute of Physical and Chemical Research), Wako-shi, Saitama, 351-0198, Japan. shunyat@riken.go.jp |
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Abstract: | reaction: see text] A new synthesis of epoxyketone 22 is described that is a key intermediate in Barton's synthesis of ovalicin (2), a powerful anti-angiogenetic inhibitor. The key process for the construction of 22 was ring-closing metathesis of olefins 11 and 12 obtained from 2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose (4) and regioselective desilylation of tri-TES ether 19. Furthermore, an alternative stereoselective route from 22 into 2 has also been developed, and the overall yield of 2 from 4 was 10.0%. |
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