The first total synthesis of 15- epi-annonin I

The first total synthesis of the 15-epimer 1b of the naturally occurring acetogenin annonin I 1a is described. All stereogenic centres in the bis-THF subunit are controlled via successive Sharpless asymmetric epoxidations (AE). Alkyl side chains were attached directly to the core using alkyne-epoxid...

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Bibliographic Details
Published inTetrahedron letters Vol. 37; no. 39; pp. 7001 - 7004
Main Authors Wöhrle, Ingo, Claßen, Arno, Peterek, Marcus, Scharf, Hans-Dieter
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.09.1996
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
(+)-BULLATACIN
SQUAMOSA
COMPLEX-I
CONFIGURATION
MODE
POTENT ANTITUMOR
INHIBITORS
ANNONACEOUS ACETOGENINS
GAMMA-LACTONES
ANNONIN-I
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Summary:The first total synthesis of the 15-epimer 1b of the naturally occurring acetogenin annonin I 1a is described. All stereogenic centres in the bis-THF subunit are controlled via successive Sharpless asymmetric epoxidations (AE). Alkyl side chains were attached directly to the core using alkyne-epoxide couplings. Starting with tosylate 3, a modular approach applying Sharpless AE is presented culminating in the synthesis of 1b.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(96)01589-4