ChemInform Abstract: Stereoselective Synthesis of Dihydropyrone-Containing Marine Natural Products. Total Synthesis and Structural Elucidation of (-)-Membrenone-C.
Abstract
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ChemInform Abstract
The total synthesis of three diastereomers of membrenone C (VIII)—(X) on similar ways is presented. Key steps are the diastereoselective aldol coupling of ketone (I), the stereoselective reduction of the carbonyl group in aldol adduct (III), and the titanium-mediated two direction aldol coupling to introduce the remaining chain carbons into dialdehyde (V). Comparison of NMR spectra and optical rotation of the three diastereomers (VIII)—(X) with a sample of naturally occurring (-)-membrenone C reveals membrenone C to have the structure of compound (VIII).
