Tetrahedron: Asymmetry

Asymmetric routes to pentadec-1-en-4-ol: application to the syntheses of aculeatins F and epi-F,(R)-and (S)-5-hexadecanolide and a formal synthesis of solenopsin

A Harbindu, BM Sharma, P Kumar

Index: Harbindu, Anand; Sharma, Brijesh M.; Kumar, Pradeep Tetrahedron Asymmetry, 2013 , vol. 24, # 5-6 p. 305 - 314

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Citation Number: 7

Abstract

A short and simple route to the synthesis of pentadec-1-en-4-ol, an important synthetic building block for the aculeatins F and epi-F, insect pheromone 5-hexadecanolide, solenopsin and various other natural products has been developed via proline-catalyzed α- aminoxylation of an aldehyde and hydrolytic kinetic resolution of a terminal epoxide. While the synthesis of aculeatins F and epi-F has been accomplished using a PIFA promoted ...