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An approach to the synthesis of pseudomonic acids

✍ Scribed by Ralph A. Raphael; John H.A. Stibbard; Raymond Tidbury

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
139 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

The synthesis of the cis-fused y-lactone 2,7-dioxabicycle-&3,4 non-4-en-g-one (3) by two routes is reported. Its stereoselective conversion to a key intermediate for pseudomonic acid synthesis is described.

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A diastereocontrolled synthesis of the tetrahydropyran nucleus of pseudomonic acids has been achieved starting from a chiral building block, which we have developed. The key step is a convex-face reduction of the block having a biased framework which allowed assemblage of the most important core in