Total Synthesis of Pyranicin
2005 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 7, no 2, 199-202 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2005. Vol. 7, no 2, 199-202 p.
horner-wadsworth-emmons, annonaceous acetogenins, antitumor agent, aldehydes, ethers
IdentifiersURN: urn:nbn:se:kth:diva-6066DOI: 10.1021/ol0479242ISI: 000226330300009ScopusID: 2-s2.0-13444249837OAI: oai:DiVA.org:kth-6066DiVA: diva2:10669
QC 201009212006-08-282006-08-282010-09-21Bibliographically approved