Issue 1, 2014

Diastereoselective vinylalumination for the synthesis of pericosine A, B and C

Abstract

The vinylalumination of α-substituted aldehydes gave anti- and syn-adducts with moderate diastereoselectivity. The diastereomeric ratio was inverted by the addition of lithium or sodium perchlorates. Thus, both anti- and syn-adducts were isolated and transformed into the biologically active conduritols, pericosine B and C, respectively. Formal synthesis of pericosine A was achieved with the anti-adduct. The rationales for the different diastereoselectivity are discussed.

Graphical abstract: Diastereoselective vinylalumination for the synthesis of pericosine A, B and C

Supplementary files

Article information

Article type
Paper
Submitted
16 Oct 2013
Accepted
29 Oct 2013
First published
31 Oct 2013

RSC Adv., 2014,4, 91-97

Diastereoselective vinylalumination for the synthesis of pericosine A, B and C

L. Li and D. Hou, RSC Adv., 2014, 4, 91 DOI: 10.1039/C3RA45871G

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