A New Stereocontrolled Total Synthesis of the Mast Cell inhibitory Alkaloid, (+)-Monanchorin, via the Wittig Reaction of a Stabilized Ylide with a Cyclic Guanidine Hemiaminal

Karl J. Hale, Liping Wang

Research output: Contribution to journalLetter

11 Citations (Scopus)

Abstract

Abstract Image

An asymmetric total synthesis of the mast cell inhibitor (+)-monanchorin is reported in which a Sharpless AD on 11 and a cyclic sulfate ring opening with an azide feature as key steps. After further manipulation, a novel guanidine-controlled ester reduction provided the guanidine-hemiaminal 25 which underwent Wittig olefination to give 27. Hydrogenation and a second guanidine-controlled reduction of the ester in 28, to obtain aldehyde 29, then set up a trifluoroacetic acid mediated cyclization to give (+)-monanchorin TFA salt.
Original languageEnglish
Pages (from-to)2154-2157
Number of pages4
JournalOrganic Letters
Volume16
Issue number8
Early online date07 Apr 2014
DOIs
Publication statusPublished - 2014

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