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Total Synthesis of the Antitumor Acetogenin Mosin B: Desymmetrization Approach to the Stereodivergent Synthesis of threo / trans / erythro ‐Type Acetogenins
Author(s) -
Maezaki Naoyoshi,
Kojima Naoto,
Sakamoto Atsunobu,
Tominaga Hiroaki,
Iwata Chuzo,
Tanaka Tetsuaki,
Monden Morito,
Damdinsuren Bazarragchaa,
Nakamori Shoji
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200390040
Subject(s) - acetogenin , desymmetrization , stereochemistry , diastereomer , chemistry , lactone , ring (chemistry) , total synthesis , polyketide , diol , absolute configuration , enantioselective synthesis , biosynthesis , organic chemistry , catalysis , medicine , annonaceae , traditional medicine , enzyme
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.