Synthetic studies of callyspongiolide: synthesis of the macrolactone core of the molecule?

Organic & Biomolecular Chemistry Pub Date: 2016-06-14 DOI: 10.1039/C6OB01007E

Abstract

A concise synthetic strategy has been developed for the synthesis of the macrolactone core 2 of a unique polyketide callyspongiolide 1. The key features of the strategy included an Evan's asymmetric alkylation, diastereoselective Michael type alkylation, Brown's asymmetric allylation reaction, an allylic alkylation of an activated Z-allylic alcohol and an intramolecular Z-selective intramolecular H–W–E olefination.

Graphical abstract: Synthetic studies of callyspongiolide: synthesis of the macrolactone core of the molecule
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