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Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

ABSTRACT: The C1-C6 region of the potent cytotoxic agent psymberin has been synthesized. The key transformations of the synthesis are an auxiliary-controlled addition of a Sn(II)-glycolate enolate to an aldehyde to yield the anti aldol product and transforming the primary alcohol into a terminal olefin utilizing organoselenium chemistry.

SUBMITTER: Pal A 

PROVIDER: S-EPMC4124943 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Asymmetric Synthesis of the C1-C6 Portion of the Psymberin Using an Evans Chiral Auxiliary.

Pal Ashutosh A   Peng Zhenghong Z   Schuber Paul T PT   Bhanu Prasad Basvoju A BA   Bornmann William G WG  

Tetrahedron letters 20131001 41

The C1-C6 region of the potent cytotoxic agent psymberin has been synthesized. The key transformations of the synthesis are an auxiliary-controlled addition of a Sn(II)-glycolate enolate to an aldehyde to yield the <i>anti</i> aldol product and transforming the primary alcohol into a terminal olefin utilizing organoselenium chemistry. ...[more]

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