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Efficient, Divergent Synthesis of Cryptophycin Unit A Analogues

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Efficient, Divergent Synthesis of Cryptophycin Unit A Analogues

Kyle L Bolduc et al. Chem Commun (Camb).

Abstract

A flexible and divergent synthesis of cryptophycin unit A analogues is described. This method relies on iridium-catalysed stereo- and enantioselective crotylation and chemoselective one-pot oxidative olefination to access common intermediate . Heck, cross metathesis, and Suzuki-Miyaura reactions are illustrated for the generation of methyl ester unit A analogues .

Figures

Figure 1
Figure 1
Cryptophycins 1 and 52 with subunits A, B, C, and D highlighted.
Scheme 1
Scheme 1
Original synthetic route to unit A and analogues developed from Eggen et al.
Scheme 2
Scheme 2
Our efficient synthesis developed for common intermediate 8.
Scheme 3
Scheme 3
Hydrolysis of methyl esters 10a-d to acids 13a-d.

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