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. 2007 Nov 8;9(23):4757-60.
doi: 10.1021/ol7020934. Epub 2007 Oct 18.

Synthesis of the C1-C52 fragment of amphidinol 3, featuring a beta-alkoxy alkyllithium addition reaction

John R Huckins  1 , Javier de Vicente, Scott D Rychnovsky
Affiliations

Synthesis of the C1-C52 fragment of amphidinol 3, featuring a beta-alkoxy alkyllithium addition reaction

John R Huckins et al. Org Lett. .

Abstract

An advanced intermediate for the synthesis of amphidinol 3 has been prepared. A cross-metathesis reaction was used to couple the C1-C12 and C13-C26 segments. An unusual beta-alkoxy alkyllithium reagent was generated from this segment and added to a Weinreb amide to assemble the C1-C52 section of amphidinol 3. These compounds represent some of the most advanced intermediates reported to date for the synthesis of amphidinol 3.

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Figures

Figure 1
Figure 1
Retrosynthetic analysis of amphidinol 3
Scheme 1
Scheme 1
Model coupling of β-alkoxy alkyllithium 6 with Weinreb amide 7
Scheme 2
Scheme 2
Synthesis of the C27-C52 Weinreb amide 2
Scheme 3
Scheme 3
Synthesis of the C14-C26 aldehyde 16 and enone 17
Scheme 4
Scheme 4
Coupling fragments to assemble the C1-C52 segment of amphidinol 3
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