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A Convergent Total Synthesis of (−)‐Mucocin: An Acetogenin from Annonaceae
Author(s) -
Hoppen Sabine,
Bäurle Stefan,
Koert Ulrich
Publication year - 2000
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 - 10.1002/1521-3765(20000703)6:13<2382::aid-chem2382>3.0.co;2-c
Subject(s) - acetogenin , computer science , programming language , biology , ecology , annonaceae
A total synthesis of the Annonaceous acetogenin mucocin has been accomplished. The synthesis follows a convergent strategy, wherein at a very late stage the left part of the molecule is connected with the right part. The key reaction is the stereocontrolled addition of an organomagnesium compound 2 to the aldehyde 3 . The THP ring of mucocin is build by a 6‐ endo epoxide cyclization of an epoxyacetonide precursor ( 16 → 17 ). The new modular synthetic approach developed herein should be useful for the synthesis of other related natural products as well as pharmacologically interesting analogues.