Total Synthesis of (+)-Neopeltolide by the Macrocyclization/Transannular Pyran Cyclization Strategy.

An 11-step synthesis of (+)-neopeltolide was developed. The C1-C7 carboxylic acid and the C8-C16 alcohol were prepared, each in six steps, from (R)- and (S)-epichlorohydrin, respectively. After esterification, our tandem macrocyclization/transannular pyran cyclization strategy was applied to a stereocontrolled construction of the neopeltolide macrolactone. The side chain was synthesized in six steps from ethyl 4-oxazolecarboxylate through palladium-catalyzed cross-couplings. A Mitsunobu reaction of the neopeltolide macrolactone and the side chain completed the synthesis.

Citation

Kazuki Nakazato, Mami Oda, Haruhiko Fuwa. Total Synthesis of (+)-Neopeltolide by the Macrocyclization/Transannular Pyran Cyclization Strategy. Organic letters. 2022 Jun 10;24(22):4003-4008

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PMID: 35649194

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