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Updated: May 18, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Stereoselective total synthesis of dinemasone A by double intramolecular hetero-Michael addition (DIHMA)
Gangavaram V M Sharma1, Gourishetty Srikanth, Pothula Purushotham Reddy
1Organic and Biomolecular Chemistry Division, Hyderabad-500 007, India. esmvee@iict.res.in
Abstract:
The first total synthesis of dinemasone A, a bioactive metabolite with a spiroketal moiety, is described. The main strategy for the construction of the spiroketal unit involves a double intramolecular hetero-Michael addition (DIHMA) of an ynone moiety. The thus obtained axial-equatorial mono anomeric spiroketal, on spiroepimerization with ZnBr(2), was converted into the requisite axial-axial double anomeric spiroketal. The ynone moiety with four stereocentres, was prepared from a chiral propargylic alcohol (C5-C11 fragment) and a dihydroxy aldehyde (C1-C4 fragment), which in turn were obtained from D-mannitol and crotyl alcohol respectively.
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