Divergence en Route to Nonclassical Annonaceous Acetogenins

Daniel Strand, Per-Ola Norrby, Tobias Rein

Research output: Contribution to journalJournal articleResearchpeer-review


Syntheses of the nonclassical annonaceous acetogenins, pyranicin, and pyragonicin from common latestage intermediates are presented. The construction of key elements relies on asymmetric HWE reactions, including the desymmetrization of a meso-dialdehyde and a parallel kinetic resolution of a racemic aldehyde. A stereoconvergent Pd-catalyzed substitution serves to install the C4 stereocenter in protected form with different orthogonal protective groups. A divergent strategy to form 1,4- and 1,6-diols, employing stereoselective Zn-mediated alkynylations, is used for completion of the core structures. Notably, the stereoselective coupling reaction toward pyragonicin proceeds with highly functionalized fragments. The methodology is further expanded by a divergent synthesis of all stereoisomers of the 2,3,6-trisubstituted tetrahydropyran subunit.
Original languageEnglish
JournalJournal of Organic Chemistry
Pages (from-to)1879-1891
Publication statusPublished - 2006


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