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Total Syntheses of Squamocin A and Squamocin D, Bi‐tetrahydrofuran Acetogenins from Annonaceae
Author(s) -
Emde Ulrich,
Koert Ulrich
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200005)2000:10<1889::aid-ejoc1889>3.0.co;2-r
Subject(s) - butenolide , acetogenin , chemistry , annonaceae , total synthesis , moiety , side chain , stereochemistry , tetrahydrofuran , enantioselective synthesis , organic chemistry , botany , catalysis , solvent , biology , polymer
The total syntheses of the Annonaceous acetogenins squamocin A and squamocin D have been achieved. The synthesis follows a modular strategy, wherein a left‐side chain, the central bis‐THF core and the right‐side chain are assembled together. Key reactions are additions of organomagnesium compounds to bi‐THF aldehydes. At the end of the synthesis the butenolide moiety was introduced. This modular synthetic approach should be useful for the synthesis of other related natural products as well as pharmacologically interesting analogs.