A convergent total synthesis of (-)-mucocin: an acetogenin from 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.
Hoppen
S
S
Institut für Chemie der Humboldt-Universität zu Berlin, Germany.
Bäurle
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S
Koert
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U
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D010946:Plants, Medicinal / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis*
D000903:Antibiotics, Antineoplastic; D005663:Furans; D007202:Indicators and Reagents; D007783:Lactones; D011714:Pyrans; C112079:isomurisolenin; C413144:mucocin