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. 2010 Jul 2;12(13):2954-7.
doi: 10.1021/ol100959a.

A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction

Mahesh P Paudyal  1 , Nigam P Rath, Christopher D Spilling
Affiliations

A formal synthesis of the C1-C9 fragment of amphidinolide C employing the Tamaru reaction

Mahesh P Paudyal et al. Org Lett. .

Abstract

Homoallylation of aldehydes with isoprene and triethylborane catalyzed by Ni(acac)(2) gave hydroxyalkenes in good yield with excellent regio- and stereoselectivity. Cross metathesis of the hydroxyalkenes with methyl acrylate using second-generation Grubbs catalyst and copper(I) iodide afforded alpha,beta-unsaturated esters, which underwent cyclization in the presence of DBU to produce tetrahydrofurans with the correct relative configuration for the C1-C9 fragment of amphidinolides C, C2, and F.

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Figures

Scheme 1
Scheme 1
Retrosynthetic analysis of amphidinolide C
Scheme 2
Scheme 2
Retrosynthetic analysis of the C1-C9 fragment
Scheme 3
Scheme 3
Synthesis of tetrahydrofuran ring
Scheme 4
Scheme 4
Homoallylation of erythrolactol
Scheme 5
Scheme 5
Cross metathesis and cyclization
Scheme 6
Scheme 6
Cross metathesis and cyclization
Scheme 7
Scheme 7
Deprotection of TBS and acetonide groups
Scheme 8
Scheme 8
Homoallylation, cross metathesis and cyclization
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