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Updated: Aug 30, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
A formal total synthesis of the salicylihalamides
Christian Herb1, Martin E Maier
1Universität Tübingen, Institut für Organische Chemie, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
Abstract:
The synthesis of the macrolactone 23 is described. The synthesis features a diastereoselective hydroboration of the chiral alkene 17 followed by a Suzuki cross-coupling reaction with the benzoate 5. The resulting seco acid 21 was converted to the macrolactone 23 by a Mitsunobu lactonization using immobilized triphenylphosphine. The stereogenic centers in the alkene 17 were established by a Noyori reduction of the beta-keto ester 8 and an Evans aldol reaction. The synthesis illustrates the conversion of a syn aldol product to the corresponding anti product by inversion of the methyl-bearing center.
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