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. 2007 Feb 15;9(4):711-4.
doi: 10.1021/ol0630447.

Diastereoselective synthesis of the pectenotoxin 2 non-anomeric AB spiroacetal

Danielle Vellucci  1 , Scott D Rychnovsky
Affiliations

Diastereoselective synthesis of the pectenotoxin 2 non-anomeric AB spiroacetal

Danielle Vellucci et al. Org Lett. .

Abstract

The reductive cyclization reaction of a cyanoacetal has been used to prepare the pectenotoxin 2 (PTX-2) AB spiroacetal with high diastereoselectively for the first time. The strategy is convergent and makes use of the axial-selective reductive lithiation of 2-cyano tetrahydropyran rings to introduce the spiroacetal center with the desired non-anomeric selectivity. [reaction: see text].

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Figures

Figure 1
Figure 1
Structures of selected pectenotoxins.
Scheme 1
Scheme 1
Retrosynthetic disconnection of the PTX-2 non-anomeric spiroacetal
Scheme 2
Scheme 2
Synthesis of the dihydropyran 4
Scheme 3
Scheme 3
Synthesis of the pectenotoxin 2 AB spiroacetal 1
Scheme 4
Scheme 4
Cyclization of the minor cyanoacetal isomer
Scheme 5
Scheme 5
Equilibration of the pectenotoxin 2 AB spiroacetal 1
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