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Catalytic Asymmetric Total Synthesis of Exiguolide
Author(s) -
Oka Kengo,
Fuchi Shunsuke,
Komine Keita,
Fukuda Hayato,
Hatakeyama Susumi,
Ishihara Jun
Publication year - 2020
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.202001773
Subject(s) - tetrahydropyran , prins reaction , catalysis , enantioselective synthesis , phosphonate , chemistry , total synthesis , stereochemistry , combinatorial chemistry , organic chemistry , ring (chemistry)
The catalytic asymmetric total synthesis of (−)‐exiguolide, a complex 20‐membered macrolide embedded with a bis(tetrahydropyran) motif, is reported. The convergent synthesis involves the construction of the C1–C11 tetrahydropyran segment via catalytic asymmetric allylation and Prins cyclization, and the formation of the C12–C21 phosphonate segment via catalytic asymmetric cyclocondensation reaction and Johnson–Claisen rearrangement. The synthesis of 15‐ epi ‐exiguolide is also described.