Sinefungin synthesis

This alkylation strategy has been successfully implemented to the diastereoselective synthesis of a number of biologically active compounds,17 19 32 72 73 including the orally active HIV protease inhibitor Crixivan (>95% de)17-19 and nucleoside antibiotic (+)-sinefungin (51) (>99% de).72 The C-6 amine stereochemistry of (+)-sinefungin was set by a highly diastereoselective allylation of (lS,2/ )-l-amino-2-indanol-derived oxazolidinone 52 (Scheme 24.10). 

The aldol reaction illustrated in eq 2 has been applied to the targeted synthesis of a number of complex molecules including Tylosin, Hapalosin, the antibiotic Sinefungin, and the HIV protease Saquinavir inhibitor. Oxazolidinone-type chiral auxiliaries derived from 1 have also been employed for the control of Diels-Alder reactions of attached acryloyl or crotonyl groups. ... 

A synthesis of sinefungin has been described, using a nitro-aldol condensation between a dialdose derived from adenosine and an -nitro-aminoacid derivative to build the required Cj Q-carbon skeleton... 

A synthesis of sinefungin (22) proceeded from a condensation of N -benzoyl-2, 3 -0-isopropylidene-adenosine 5 -aldehyde with nitromethane, the nitroaldol then being reduced to the corresponding 5, 6 -dideoxy-6 -nitro derivative, which was further condensed with an L-aspartic acid derivative leading to (22) and its 75... 

A synthesis of sinefungin (29) and its 6 -epimer has been reported, which uses the adenosine-based thiopyridinyl ester (30). This underwent photchemical reaction with the alkene (31) to form the skeleton required for the products (Scheme 6). 

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