Total Synthesis of Pyranicin

A stereocontrolled convergent synthesis of the annonaceous acetogenin pyranicin (1) is presented. Asymmetric Horner−Wadsworth−Emmons (HWE) reactions were used to access key intermediates. The tetrahydropyran derivative 2 was obtained via an asymmetric desymmetrization of the meso-dialdehyde 6, and t...

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Bibliographic Details
Published in:Organic letters 2005-01, Vol.7 (2), p.199-202
Main Authors: Strand, Daniel, Rein, Tobias
Format: Article
Language:English
Subjects:
aldehydes
annonaceous acetogenins
antitumor agent
Catalysis
Chemistry
ethers
Furans - chemical synthesis
horner-wadsworth-emmons
Kemi
Lactones - chemical synthesis
Molecular Structure
NATURAL SCIENCES
NATURVETENSKAP
Organic chemistry
Organisk kemi
Palladium - chemistry
Stereoisomerism
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Summary:A stereocontrolled convergent synthesis of the annonaceous acetogenin pyranicin (1) is presented. Asymmetric Horner−Wadsworth−Emmons (HWE) reactions were used to access key intermediates. The tetrahydropyran derivative 2 was obtained via an asymmetric desymmetrization of the meso-dialdehyde 6, and the butenolide fragment was constructed using a stereoconvergent reaction sequence involving a parallel kinetic HWE resolution followed by a Pd-catalyzed allylic substitution. The C10/C15 1,6-diol motif was installed using Carreira's asymmetric acetylide addition methodology.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol0479242