Synthetic Studies towards Pectenotoxin-2: Synthesis of the Nonanomeric 10-epi-ABCDE Ring Segment by Kinetic Spiroketalization

Jatta E. Aho, Antti Piisola, K. Syam Krishnan, Petri M. Pihko*

*Corresponding author for this work

    Research output: Contribution to journalArticleScientificpeer-review

    18 Citations (Scopus)

    Abstract

    The synthesis of the nonanomeric 10-epi-ABCDE ring system of pectenotoxin-2 has been achieved by using a kinetic spiroketalization reaction. The synthesis of the spiroketalization precursor was achieved through a cross-metathesis/hydrogenation sequence. The formation of the epi-C10 isomer resulted from an unexpected anti-Felkin selective addition of organometallic nucleophiles to the advanced CDE ring precursor. This addition reaction was investigated with differently protected alpha,beta-dioxygenated model aldehydes, which displayed similar anti-Felkin selectivities with organometallic nucleophiles.

    Original languageEnglish
    Pages (from-to)1682-1694
    Number of pages13
    JournalEuropean Journal of Organic Chemistry
    Issue number9
    DOIs
    Publication statusPublished - Mar 2011
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Natural products
    • Spiro compounds
    • Anomeric effect
    • Enantioselectivity
    • Chirality
    • FATTY-ACID ESTERS
    • DIARRHETIC SHELLFISH TOXINS
    • MUSSELS MYTILUS-EDULIS
    • PART II
    • STEREOCONTROLLED CYCLIZATION
    • ALKOXIDE PRECOORDINATION
    • CONVENIENT SYNTHESIS
    • ASYMMETRIC SYNTHESES
    • GREENSHELL MUSSELS
    • DINOPHYSIS-ACUTA

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