Diastereoselective vinylalumination for the synthesis of pericosine A, B and C?
RSC Advances Pub Date: 2013-10-31 DOI: 10.1039/C3RA45871G
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.
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Journal Name：RSC Advances
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CAS no.: 89640-58-4
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