Total Synthesis of the Antitumor Acetogenin Mosin B: Desymmetrization Approach to the Stereodivergent Synthesis of threo/trans/erythro‐Type Acetogenins
- 16 January 2003
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 9 (2) , 389-399
- https://doi.org/10.1002/chem.200390040
Abstract
A total synthesis of the threo/trans/erythro-type acetogenin mosin B and one of its diastereomers has been achieved. The carbon skeleton is assembled in a convergent fashion from two segments (a THF ring segment and a γ-lactone segment) through the Nozaki–Hiyama–Kishi reaction. The THF ring segment was stereoselectively constructed by a stereodivergent synthesis starting from a common intermediate (4-cyclohexene-1,2-diol) based on a desymmetrization strategy. The γ-lactone segment was synthesized by coupling a triflate and a chiral α-sulfenyl γ-lactone. By virtue of these synthetic results, we suggest that the absolute configuration of natural mosin B is 1 a. Antiproliferative effects of 1 a and 1 b were also investigated.Keywords
This publication has 32 references indexed in Scilit:
- C2-Symmetric Bis-sulfoxide: A Novel Chiral Auxiliary for Asymmetric Desymmetrization of Cyclic meso-1,2-DiolsThe Journal of Organic Chemistry, 2000
- Comparison of Ectoparasites Infestation for Fresh and Saltwater Fishes from Euphrates, and Razzaza Lake, IraqJournal of Natural Products, 1999
- Asymmetric Dihydroxylation−Haloetherification Strategy for the Synthesis of Tetrahydrofuran-Containing AcetogeninsThe Journal of Organic Chemistry, 1998
- Enantioselective Total Synthesis of (+)-6-epi-Mevinolin and Its Analogs. Efficient Construction of the Hexahydronaphthalene Moiety by High Pressure-Promoted Intramolecular Diels−Alder Reaction of (R,2Z,8E,10E)-1-[(tert-Butyldimethylsilyl)oxy]-6-methyl-2,8,10-dodecatrien-4-oneThe Journal of Organic Chemistry, 1997
- 1,5-Benzodithiepan-3-one 1,5-dioxide: A novel chiral auxiliary for asymmetric desymmetrization of meso-1,2-diolsTetrahedron: Asymmetry, 1996
- Acetal Templates for the Synthesis of trans-2,5-Disubstituted TetrahydrofuransThe Journal of Organic Chemistry, 1995
- Mitochondrial respiratory chain inhibitors induce apoptosisFEBS Letters, 1994
- Annonaceous Acetogenins from the Seeds of Annona squamosa. Non-adjacent Bis-tetrahydrofuranic Acetogenins.CHEMICAL & PHARMACEUTICAL BULLETIN, 1994
- Annonaceous Acetogenins: A ReviewJournal of Natural Products, 1990
- Total synthesis of (+)-ophiobolin CJournal of the American Chemical Society, 1989