Total Synthesis of the Antitumor Acetogenin Mosin B: Desymmetrization Approach to the Stereodivergent Synthesis of  threo / trans / erythro ‐Type Acetogenins | Zendy

Maezaki Naoyoshi | Zendy; Kojima Naoto | Zendy; Sakamoto Atsunobu | Zendy; Tominaga Hiroaki | Zendy; Iwata Chuzo | Zendy; Tanaka Tetsuaki | Zendy; Monden Morito | Zendy; Damdinsuren Bazarragchaa | Zendy; Nakamori Shoji | Zendy

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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.

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