Design, synthesis and antiproliferative activity of styryl lactones related to (+)-goniofufurone.

This paper describes a straightforward divergent synthesis of (+)-goniofufurone mimics (4, 5 and 6) starting from d-xylose. In a preliminary bioassay, analogues 4 and 5 exhibited a submicromolar antiproliferative activity towards HL-60 cells, while the corresponding parent compound 1 was completely inactive against this cell line. At the same time, these molecules showed approximately 10-fold stronger cytotoxicity in the same cell line when compared to the standard anticancer drug doxorubicin (DOX).

Design, synthesis and antiproliferative activity of two new heteroannelated (-)-muricatacin mimics.

Two new (-)-muricatacin mimics bearing a furano-furanone ring and an oxygen isostere in the side chain have been designed and synthesized and their in vitro antiproliferative activity was evaluated against several human tumour cell lines. Both analogues showed an increased activity against HL-60 cells with 17- and 185-fold higher potency than (-)-muricatacin. A straightforward synthesis of (-)-muricatacin is also disclosed.

Synthesis and antiproliferative activity of unnatural enantiomers of 7-epi-goniofufurone and crassalactone C.

A facile synthesis of 7-epi-(-)-goniofufurone as well as the first synthesis of (-)-crassalactone C was achieved starting from D-xylose. A comparison of their in vitro antitumour activities with those observed for the corresponding naturally occurring enantiomers was provided.

Divergent synthesis of cytotoxic styryl lactones from D-xylose. The first total synthesis of (+)-crassalactone C.

A new divergent approach to (+)-goniofufurone (1) and 7-epi-(+)-goniofufurone (2), as well as the first total synthesis of crassalactone C (3), has been achieved starting from D-xylose. In a preliminary bioassay, all three natural products 1, 2, and 3 showed remarkable in vitro antiproliferative activities against K562, Raji, and HeLa neoplastic cell lines.

Synthesis and antitumour activity of new muricatacin and goniofufurone analogues.

A divergent approach to the 7-oxa (-)-muricatacin analogue 2, the corresponding (+)-enantiomer ent-2 and the furanolactone 3 is reported starting from D-xylose. The resulting lactones have shown a potent and selective in vitro cytotoxicity against certain human neoplastic cell lines.

Regiochemistry of epoxide ring opening in methyl 2,3-anhydro-4-azido-4-deoxy-alpha- and beta-L-lyxopyranosides.

Methyl 2,3-anhydro-4-O-methanesulfonyl-alpha-d-ribopyranoside (12) was prepared through a new six-step sequence starting from d-arabinose. Chemical behaviour of 12 was further studied under solvolytic conditions and in the presence of azide anion as a nucleophile. Factors governing the regiochemistry of epoxide ring opening are briefly discussed.