An alternative stereoselective total synthesis of (-)-pyrenophorol

The total synthesis of 16-membered C 2 -Symmetric dilactone (-)-Pyrenophorol was accomplished starting from commercially available (S)-epoxide prepared by hydrolytic kinetic resolution of (±) - epoxide with key steps of Grignard reaction, Swern oxidation, Wittig reaction and cyclization was achieved...

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Bibliographic Details
Published in:Natural product research 2019-10, Vol.33 (19), p.2738-2743
Main Authors: Alluraiah, Gurrala, Sreenivasulu, Reddymasu, Chandrasekhar, Choragudi, Raju, Rudraraju Ramesh
Format: Article
Language:English
Subjects:
(-)-pyrenophorol
(S)-epoxide
Grignard reactions
mitsunobu cyclization
Oxidation
Stereoselectivity
swern oxidation
wittig reaction
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Summary:The total synthesis of 16-membered C 2 -Symmetric dilactone (-)-Pyrenophorol was accomplished starting from commercially available (S)-epoxide prepared by hydrolytic kinetic resolution of (±) - epoxide with key steps of Grignard reaction, Swern oxidation, Wittig reaction and cyclization was achieved by intermolecular Mitsunobu cyclization. The synthesis of (-)-Pyrenophorol accomplished from cheaply available starting material, easily work-up procedures and reduction of cost in industrial process were major advantages of this route.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2018.1499636