Sakaguchi synthesis, amathaspiramide

Amathaspiramide F has also been synthesized by Sakaguchi and coworkers [64, 65], and they started the synthesis by taking a-hydroxy-a-ethynylsilane as a starting material. The key step of the synthesis was enolate Claisen rearrangement. While ( )-amathaspiramide F has been synthesized by Soheili and Tambar [66]. They started the synthesis by taking substituted phenyl allyl carbonate and A-substituted proline ester. 

Since the isolation of the amathaspiramides in 1999, there have been efforts by various groups toward their total synthesis. In 2002, Trauner reported the first synthesis of a member of this alkaloid family, (—)-amathaspiramide F. The Sakaguchi group followed in 2008 with their own completed synthesis of (—)-amathaspiramide F. It was not until 2012 that other members of the amathaspiramide family were synthesized. The Fukuyama group completed the syntheses of the entire family (amathaspiramides A-F). ... 

In the Sakaguchi group s total synthesis of ( )-amathaspiramide F, the key disconnection to generate the two contiguous stereocenters was based on an enolate Claisen rearrangement of aminoester 5, which could be derived enan-tioselectively from arylpropargyl alcohol 15 (Scheme 5). 

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