Abstract
A convenient and practical strategy for the construction of a natural amino sugar analogue, furanodictine B, isolated from the multicellular fruit body has been developed in an optically active form. The synthetic process is based on readily accessible and stereodefined manipulation of the highly functionalized bicyclic derivative incorporating the glucuronolactone-derived skeleton.
Key words
natural product - furanodictine - 3,6-anhydrosugar - amino sugar - glucuronolactone
References
1
Kikuchi H.
Saito Y.
Komiya J.
Takaya Y.
Honma S.
Nakahata N.
Ito A.
Oshima Y.
J. Org. Chem.
2001,
66:
6982
2
Maeda Y.
Inouye K.
Takeuchi I.
Dictyostelium: A Model System for Cell and Developmental Biology, Frontiers Science Series No. 21
Universal Academy Press Inc.;
Tokyo:
1997.
3
Yoda H.
Suzuki Y.
Takabe K.
Tetrahedron Lett.
2004,
45:
1599
4 During our synthetic studies of these substances, the synthetic approach to the intermediate of furanodictine B(2) starting from d-glucose has just appeared. See: Mereyala HB.
Baseeruddin M.
Koduru SR.
Tetrahedron: Asymmetry
2004,
15:
3457
5a
Martinelli MJ.
Vaidyanathan R.
Khau VV.
Tetrahedron Lett.
2000,
41:
3773
5b
Martinelli MJ.
Nayyar NK.
Moher ED.
Dhokte UP.
Pawlak JM.
Vaidyanathan R.
Org. Lett.
1999,
1:
447
6 Direct deoxgenation with Et3SiH-Lews acid system after reduction of the lactone 4 to the corresponding lactol derivative, however, resulted in the preparation of the complex mixture.
7a
Homer L.
Gross A.
Justus Liebigs Ann. Chem.
1955,
591:
117
7b
Hankovszky HO.
Hideg K.
Lex L.
Synthesis
1981,
147
7c For recent examples, see: Lucas S.
Luther LM.
Burke SD.
Org. Lett.
2004,
6:
2965
7d See also: Eipert M.
Maichle-Moessmer C.
Maier ME.
Tetrahedron
2003,
59:
7949
8
Yoda H.
Nakaseko Y.
Takabe K.
Tetrahedron Lett.
2004,
45:
4217 ; and references cited therein
9 Synthesized furanodictine B in this report was a mixture [α:β = 1:2.4 (natural; α:β = 2:3)1] of the two anomers.